2-amino-N-(4-chlorophenyl)-5-methylbenzamide → HCID 10411684, compound

HRID 844185Notes

Reaction equation

HRID 844185 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:18])[C:10]2[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:11]=2[NH2:17])=[CH:4][CH:3]=1.Cl[C:20]([C:22]1[S:26][C:25]2[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=2[C:23]=1[Cl:31])=[O:21]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:18])[C:10]2[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:11]=2[NH:17][C:20]([C:22]2[S:26][C:25]3[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=3[C:23]=2[Cl:31])=[O:21])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 3351702-amino-N-(4-chlorophenyl)-5-methylbenzamideHCID 5198983-Chlorobenzo(b)thiophene-2-carbonyl chloride

Product 1

HCID 10411684HCID 10411684, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of N-(4-chlorophenyl)-2-amino-5-methylbenzamide (0.11 g, 0.42 mmol) in pyridine (5 mL) at 0° C. was added 2-chlorocarbonyl-3-chlorobenzo[b]thiophene (0.15 g, 0.64 mmol), and the mixture allowed to warm to ambient temperature with stirring. After 16 hours, the mixture was poured onto water (5 mL) and the resulting white solid collected by filtration and dried in vacuo. Recrystallization from acetonitrile afforded 0.095 g (50% yield) of N-(4-chlorophenyl)-2-[((3-chlorobenzo[b]thien-2-yl)carbonyl)amino]-5-methylbenzamide, as a white crystalline solid; NMR (DMSO-d6/TFA) 11.4 (s, 1), 10.7 (s, 1), 8.2 (d, 1), 7.4-8.2 (m, 10), 2.4 (s, 3) ppm.

Workup

  1. additionthe mixture was poured onto water (5 mL)
  2. filtrationthe resulting white solid collected by filtration
  3. customdried in vacuo
  4. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-33cbd5dee59a44be8731010a5c7904ab
Source dataset
uspto-grants-2002_04
Patent number
US06380221B1

Reaction notes

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