Water → HCID 66771755, compound

HRID 1645315Notes

Reaction equation

C1C(=O)N([Br:8])C(=O)C1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[S:21][C:20]3[CH:22]=[C:23]([O:26][C:27](=[O:33])[N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])[CH:24]=[CH:25][C:19]=3[CH:18]=2)=[CH:13][CH:12]=1.O>C1COCC1>[Br:8][C:18]1[C:19]2[CH:25]=[CH:24][C:23]([O:26][C:27](=[O:33])[N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])=[CH:22][C:20]=2[S:21][C:17]=1[C:14]1[CH:13]=[CH:12][C:11]([O:10][CH3:9])=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Add NBS (7.37 g, 40.99 mmoles) to the solution of diethyl-carbamic acid 2-(4-methoxy-phenyl)-benzo[b]thiophen-6-yl ester in THF at ambient temperature. Stir the mixture for 20 minutes. Distill the resulting solution to 47 mL. Add Methanol (15 mL) to the distilled solution and cool the solution to 50° C. Add seed crystals of Example 2 (340 mg, 0.8 mmoles) to the cooled solution and stir the mixture for 15 minutes. Slowly add water (35 mL). Allow the mixture to cool to ambient temperature, and hold at ambient temperature for one hour. Collect the product by vacuum filtration, wash with aqueous THF (30 mL, 2 water: 1 THF) and dry in a vacuum oven to yield diethyl-carbamic acid 3-bromo-2-(4-methoxy-phenyl)-benzo[b]thiophen-6-yl ester. Yield 15.75 g (36.26 mmol, 93% of theory).

Workup

distillationDistill the resulting solution to 47 mL
stirringstir the mixture for 15 minutes
temperatureAllow the mixture to cool to ambient temperature
waithold at ambient temperature for one hour
customCollect the product
filtrationby vacuum filtration
washwash with aqueous THF (30 mL, 2 water: 1 THF)
customdry in a vacuum oven

Sources & evidence

ORD record: ord-cb27c146c1954e4f85c898578caf28ef
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08124776B2

Reaction notes

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