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

HRID 370115Notes

Reaction equation

HRID 370115 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-3c8a4d0cc0714af8a90870afe22e5c6c
Source dataset
uspto-grants-2000_10
Patent number
US06140351

Reaction notes

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