p-Chlorophenacyl bromide → HCID 71536626, compound

HRID 1519269Notes

Reaction equation

HRID 1519269 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][CH:28]=1)=O>O>[Cl:33][C:30]1[CH:31]=[CH:32][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:28][CH:29]=1

Participants

4

Reactant 2

HCID 68303p-Chlorophenacyl bromideHCID 866798322'-Nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester2×

Product 1

HCID 71536626HCID 71536626, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-[4-(4-Chloro-phenyl)-thiazol-2-yl]-2′-nitro-biphenyl-2-carboxylic acid (59 mg, 21%) 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-4′-chloroacetophenone (available from Alfa Aesar) 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 13.12 (br s, 1H), 8.57 (s, 1H), 8.33 (s, 1H), 8.26 (d, J=8.8 Hz, 1H), 8.09-8.16 (m, 3H), 7.41-7.79 (m, 6H).

Workup

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

Sources & evidence

ORD record
ord-4ea552cc219b430290d52d72208f720a
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

Loading…