Acetic Acid → HCID 67293569, compound
Reaction equation
Br[C:2]1[S:6][C:5]([C:7]2[S:8][C:9]3[N:10]=[C:11]([C:15]4[S:16][C:17](Br)=[C:18]([Br:34])[C:19]=4[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[S:12][C:13]=3[N:14]=2)=[C:4]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[C:3]=1[Br:50].Cl.C(O)(=O)C.C(O)C>[Zn].C1(C)C=CC=CC=1>[Br:50][C:3]1[C:4]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])=[C:5]([C:7]2[S:8][C:9]3[N:10]=[C:11]([C:15]4[S:16][CH:17]=[C:18]([Br:34])[C:19]=4[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[S:12][C:13]=3[N:14]=2)[S:6][CH:2]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
To a 50 mL round bottom flask were added to 0.800 g of 2,5-bis(5,4 dibromo-3-tetradecyl-2-thienyl)-thiazolo[5,4-d]thiazole, 0.500 g Zn dust, 3 mL 3 M HCl, 2 mL acetic acid, 15 mL ethanol, and 15 mL toluene. The flask was heated to 100° C. for 3 hours. The reaction mixture was then filtered and the solvents were removed by rotary evaporation. The residue was purified by column chromatography using a mixture of hexane and dichloromethane to give the desired compound. The NMR data were obtained and were consistent with those of the desired compound.
Workup
- filtrationThe reaction mixture was then filtered
- customthe solvents were removed by rotary evaporation
- customThe residue was purified by column chromatography
- additiona mixture of hexane and dichloromethane
Sources & evidence
- ORD record
- ord-cc57dee68c6747f2bfb742d4fbfb83ea
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09337358B2
Reaction notes
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