2-Bromo-1-(2,4-dichlorophenyl)ethan-1-one → HCID 71537195, compound

HRID 1519267Notes

Reaction equation

HRID 1519267 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][C:30]([Cl:33])=[CH:29][C:28]=1[Cl:34])=O>>[Cl:34][C:28]1[CH:29]=[C:30]([Cl:33])[CH:31]=[CH:32][C:27]=1[C:25]1[N:12]=[C:11]([C:9]2[CH:10]=[C:5]([C:3]([OH:2])=[O:4])[C:6]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N+:20]([O-:22])=[O:21])=[CH:7][CH:8]=2)[S:13][CH:24]=1

Participants

3

Reactant 2

HCID 758282-Bromo-1-(2,4-dichlorophenyl)ethan-1-oneHCID 866798322'-Nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester2×

Product 1

HCID 71537195HCID 71537195, compoundYield 8%

Procedure

4-[4-(2,4-Dichloro-phenyl)-thiazol-2-yl]-2′-nitro-biphenyl-2-carboxylic acid (24 mg, 8%) was prepared from 2′-nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester (which may be prepared as described for Intermediate 4) and 2-bromo-2′,4′-dichloroacetophenone (available from Oakwood Products, Inc.) using the procedure described for the preparation of Example 1. 1H NMR (300 MHz, DMSO-d6) δ 13.16 (s, 1H), 8.55 (d, J=1.4 Hz, 1H), 8.29 (s, 1H), 8.23 (d, J=8.0 Hz, 1H), 8.14 (d, J=7.9 Hz, 1H), 8.05 (d, J=8.4 Hz, 1H), 7.57-7.78 (m, 4H), 7.43 (t, J=8.3 Hz, 2H).

Workup

  1. customdescribed for the preparation of Example 1

Sources & evidence

ORD record
ord-3cfddfa944af4f5188571cb9e0a5847f
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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