2-Bromo-1-(3,4-dichlorophenyl)ethanone → HCID 71506886, compound

HRID 1519271Notes

Reaction equation

HRID 1519271 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])=[C:29]([Cl:34])[CH:28]=1)=O>>[Cl:34][C:29]1[CH:28]=[C:27]([C:25]2[N:12]=[C:11]([C:9]3[CH:10]=[C:5]([C:3]([OH:2])=[O:4])[C:6]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[N+:20]([O-:22])=[O:21])=[CH:7][CH:8]=3)[S:13][CH:24]=2)[CH:32]=[CH:31][C:30]=1[Cl:33]

Participants

3

Reactant 2

HCID 2447512-Bromo-1-(3,4-dichlorophenyl)ethanoneHCID 866798322'-Nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester2×

Product 1

HCID 71506886HCID 71506886, compoundYield 37%

Procedure

4-[4-(3,4-Dichloro-phenyl)-thiazol-2-yl]-2′-nitro-biphenyl-2-carboxylic acid (109 mg, 37%) 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-3′,4′-dichloroacetophenone (available from Oakwood Products, Inc.) using the procedure described for the preparation of Example 1. The compound of Example 15 has the same formula as the compound of Example 16. 1H NMR (300 MHz, DMSO-d6) δ 13.18 (s, 1H), 8.56 (s, 1H), 8.47 (s, 1H), 8.26-8.32 (m, 2H), 8.15 (d, J=8.2 Hz, 1H), 8.07 (d, J=8.4 Hz, 1H), 8.03 (d, J=8.6 Hz, 1H), 7.41-7.81 (m, 5H).

Workup

  1. customdescribed for the preparation of Example 1

Sources & evidence

ORD record
ord-f8f1ad77a8204d8b8d1d9e324b0121ed
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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