Phenacyl bromide → HCID 71536084, compound

HRID 1519300Notes

Reaction equation

HRID 1519300 reaction equation
C[O:2][C:3]([C:5]1[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N+:20]([O-:22])=[O:21])=[CH:7][CH:8]=[C:9]([C:11](=[S:13])[NH2:12])[CH:10]=1)=[O:4].Br[CH2:24][C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=O>O>[N+:20]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:6]1[C:5]([C:3]([OH:2])=[O:4])=[CH:10][C:9]([C:11]2[S:13][CH:24]=[C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:12]=2)=[CH:8][CH:7]=1)([O-:22])=[O:21]

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 866798322'-Nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester2×

Product 1

HCID 71536084HCID 71536084, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2′-Nitro-4-(4-phenyl-thiazol-2-yl)-biphenyl-2-carboxylic acid (100 mg, 39%) was prepared from 2′-nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester (which may be prepared as described for Intermediate 4) and 2-bromoacetophenone (available from Chem-Impex International, Inc.) using the procedure described for the preparation of Example 18 except that the entire 4 mL of water was added at the beginning of the hydrolysis step rather than being added in two portions. 1H NMR (300 MHz, DMSO-d6) δ 13.16 (br s, 1H), 8.58 (d, J=1.9 Hz, 1H), 8.06-8.28 (m, 5H), 7.36-7.82 (m, 7H).

Workup

  1. additionwas added at the beginning of the hydrolysis step rather
  2. additionthan being added in two portions

Sources & evidence

ORD record
ord-e4e148478ce84fa491b964f07ef3d3bf
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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