Phosphorus oxychloride → HCID 66668846, compound
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[S:14][C:13]([NH2:15])=[N:12][N:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[Cl:16][C:17](=O)[CH2:18][C:19](OC)=[O:20].O=P(Cl)(Cl)Cl.CCN(C(C)C)C(C)C>CC#N>[Cl:16][C:17]1[N:15]=[C:13]2[S:14][C:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)=[N:11][N:12]2[C:19](=[O:20])[CH:18]=1Participants
Procedure
In a particular instance, the compound of this example is prepared as described or similarly described as follows: To 5-(3-nitrophenyl)-1,3,4-thiadiazol-2-amine (2) (3.0 g, 13.50 mmol) in MeCN (120 ml) is added methyl 3-chloro-3-oxopropanoate (1.735 mL, 16.20 mmol). The mixture is stirred at room temperature for 2 hours. After consumption of the starting material, POCl3 (60 mL, 644 mmol) is added along with DIPEA (2.358 mL, 13.50 mmol) in MeCN (10 mL). The mixture is heated in the microwave at 150° C. for 25 min, cooled, and concentrated in vacuo. The resulting slurry is taken up in chloroform, poured over ice and washed with saturated NaHCO3, water and brine, dried over MgSO4, and concentrated in vacuo to give a dark red oil which is purified via column chromatography on a 100 g snap column with 0-10% EtOAc/DCM gradient elution to give 7-chloro-2-(3-nitrophenyl)-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one (1.36 g, 4.41 mmol, 32.6% yield) as an orange solid.
Workup
- temperatureThe mixture is heated in the microwave at 150° C. for 25 min
- temperaturecooled
- concentrationconcentrated in vacuo
- additionpoured over ice
- washwashed with saturated NaHCO3, water and brine
- dry with materialdried over MgSO4
- concentrationconcentrated in vacuo
- customto give a dark red oil which
- customis purified via column chromatography on a 100 g snap column with 0-10% EtOAc/DCM gradient elution
Sources & evidence
- ORD record
- ord-6b17d660eb8a46fc9d1072c8dac34e33
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09066948B2
Reaction notes
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