4-(Bromoacetyl)benzonitrile → HCID 71537193, compound

HRID 1519293Notes

Reaction equation

HRID 1519293 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].[C:23]([C:25]1[CH:34]=[CH:33][C:28]([C:29](=O)[CH2:30]Br)=[CH:27][CH:26]=1)#[N:24]>>[C:23]([C:25]1[CH:34]=[CH:33][C:28]([C:29]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:30]=2)=[CH:27][CH:26]=1)#[N:24]

Participants

3

Reactant 2

HCID 986544-(Bromoacetyl)benzonitrileHCID 866798322'-Nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester2×

Product 1

HCID 71537193HCID 71537193, compoundYield 37%

Procedure

4-[4-(4-Cyano-phenyl)-thiazol-2-yl]-2′-nitro-biphenyl-2-carboxylic acid (100 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 4-cyanophenacyl bromide (available from Oakwood Products, Inc.) using the procedure described for the preparation of Example 1. 1H NMR (300 MHz, DMSO-d6) δ 8.44-8.47 (m, 2H), 8.27 (d, J=8.5 Hz, 2H), 7.94-8.00 (m, 4H), 7.63-7.68 (m, 1H), 7.47-7.52 (m, 1H), 7.28 (dd, J=7.6, 1.4 Hz, 1H), 7.20 (d, J=7.9 Hz, 1H).

Workup

  1. customdescribed for the preparation of Example 1

Sources & evidence

ORD record
ord-5f8c2dc0a2e24a228e70c0dd00bacb08
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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