Tetrahydrofuran → HCID 87941504, compound
Reaction equation
[CH:1]1[C:30]2[C:5](=[N:6][C:7]3[C:8]4[C:17]([C:18]5[C:27]([C:28]=3[N:29]=2)=[N:26][C:25]2[C:20](=[CH:21][C:22]([C:31](Cl)=[O:32])=[CH:23][CH:24]=2)[N:19]=5)=[N:16][C:15]2[C:10](=[CH:11][C:12]([C:34](Cl)=[O:35])=[CH:13][CH:14]=2)[N:9]=4)[CH:4]=[CH:3][C:2]=1[C:37](Cl)=[O:38].[CH2:40]([O:52][C:53]1[CH:54]=[C:55]([CH:60]=[C:61]([O:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH2:83][CH2:84][CH2:85][CH2:86][CH2:87][CH3:88])[C:62]=1[O:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH3:75])[C:56]([NH:58][NH2:59])=[O:57])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51].[CH2:89]1[CH2:93][O:92][CH2:91][CH2:90]1>>[CH2:40]([O:52][C:53]1[CH:54]=[C:55]([CH:60]=[C:61]([O:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH2:83][CH2:84][CH2:85][CH2:86][CH2:87][CH3:88])[C:62]=1[O:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH3:75])[C:56]([N:58]([C:31]([C:22]1[CH:23]=[CH:24][C:25]2[C:20]([CH:21]=1)=[N:19][C:18]1[C:17]3[C:8]([C:7]4[N:6]=[C:5]5[C:30]([CH:1]=[C:2]([C:37]([N:58]([C:56](=[O:57])[C:55]6[CH:60]=[C:61]([O:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH2:83][CH2:84][CH2:85][CH2:86][CH2:87][CH3:88])[C:62]([O:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH3:75])=[C:53]([O:52][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[CH:54]=6)[NH2:59])=[O:38])[CH:3]=[CH:4]5)=[N:29][C:28]=4[C:27]=1[N:26]=2)=[N:9][C:10]1[C:15](=[CH:14][CH:13]=[C:12]([C:34]([N:58]([C:56](=[O:57])[C:55]2[CH:54]=[C:53]([O:52][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[C:89]([O:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH3:75])=[C:93]([O:92][CH2:91][CH2:90][CH2:86][CH2:85][CH2:84][CH2:83][CH2:82][CH2:81][CH2:80][CH2:79][CH2:78][CH3:77])[CH:60]=2)[NH2:59])=[O:35])[CH:11]=1)[N:16]=3)=[O:32])[NH2:59])=[O:57])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51]Participants
Conditions
- Temperature
- 0 °C
Procedure
The title compound was synthesized according to a modified literature procedure.29 It should be noted that a mixture of the 2,8,14 and 2,8,15 isomers are formed. 5,6,11,12,17,18-Hexaazatrinaphthylene 2,8,14-tricarbonyl trichloride BK1—17 (2.28 g, 3.99 mmol) was dissolved in 80 ml dry THF and placed in a 100 ml three neck round bottom flask. 3,4,5-Tris(dodecanyloxy)benzoichydrazide SM6 (9.07 g, 13.2 mmol), dissolved in 200 ml THF, was placed in a dropping funnel. The apparatus was placed in a dewar flask (ice+H2O). The apparatus was degassed with argon. At a steady rate, SM6 solution was slowly added dropwise. The reaction mixture was stirred at 0° C. for two hours, after which 3 ml of pyridine were added and the solution was further stirred at room temperature overnight. Water (200 ml) was added to the reaction mixture upon which a dark solid formed. This solid (10.0 g, 99%) was filtered and dried. This compound was used with no further purification.
Workup
- additionshould be noted that a mixture of the 2,8,14 and 2,8,15 isomers
- customare formed
- customwas placed in a dropping funnel
- customThe apparatus was placed in a dewar flask
- customThe apparatus was degassed with argon
- additionAt a steady rate, SM6 solution was slowly added dropwise
- additionafter which 3 ml of pyridine were added
- stirringthe solution was further stirred at room temperature overnight
- additionWater (200 ml) was added to the reaction mixture upon which a dark solid
- customformed
- filtrationThis solid (10.0 g, 99%) was filtered
- customdried
- customThis compound was used with no further purification
Sources & evidence
- ORD record
- ord-5a4fa34d048041da80534be11bc743d1
- Source dataset
- uspto-grants-2011_08
- Patent number
- US07994423B2
Reaction notes
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