1-Chloro-4-(chloromethyl)benzene → HCID 71295122, compound

HRID 1776925Notes

Reaction equation

HRID 1776925 reaction equation
[Br:1][C:2]1[C:3]([NH:22][S:23]([CH3:26])(=[O:25])=[O:24])=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)=[C:7]([C:17]([NH:19][CH3:20])=[O:18])[C:6]=2[CH:21]=1.[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34]Cl)=[CH:30][CH:29]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[C:3]([N:22]([CH2:34][C:31]2[CH:32]=[CH:33][C:28]([Cl:27])=[CH:29][CH:30]=2)[S:23]([CH3:26])(=[O:24])=[O:25])=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:11]=[CH:12][C:13]([F:16])=[CH:14][CH:15]=3)=[C:7]([C:17]([NH:19][CH3:20])=[O:18])[C:6]=2[CH:21]=1

Participants

5

Reactant 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 11430Potassium CarbonateHCID 67393824HCID 67393824, compound

Product 1

HCID 71295122HCID 71295122, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-bromo-2-(4-fluorophenyl)-N-methyl-6-(methylsulfonamido)benzofuran-3-carboxamide (0.55 g, 1.25 mmol), 1-chloro-4-(chloromethyl)benzene (0.24 g, 1.5 mmol), K2CO3 (0.35 g, 2.5 mmol) and KI (0.25 g, 0.15 mmol) in DMF (10 mL) was stirred at 80° C. for 2 hours. The mixture was concentrated in vacuo and the resulting residue was washed by H2O and filtered to provide the white solid 5-bromo-6-(N-(4-chlorobenzyl)methylsulfonamido)-2-(4-fluorophenyl)-N-methylbenzofuran-3-carboxamide without further purification. 1H-NMR (CDCl3, 400 MHz) δ 8.14 (s, 1H), 7.81˜7.84 (m, 2H), 7.15˜7.25 (m, 7H), 5.79 (br s, 1H), 5.15 (d, J=7.4 Hz, 1H), 4.55 (d, J=7.4 Hz, 1H), 3.10 (s, 3H), 2.96 (d, J=4.8 Hz, 3H). MS (M+H)+: 565/567.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. washthe resulting residue was washed by H2O
  3. filtrationfiltered

Sources & evidence

ORD record
ord-de000e1cd0ad46cc91574ba4c44a8bca
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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