Pyridine → 3-{[(5-Chloro-3-methyl-1-benzothien-2-yl)sulfonyl]amino}benzoic acid

HRID 589706Notes

Reaction equation

HRID 589706 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10](Cl)(=[O:12])=[O:11])=[C:7]([CH3:14])[C:6]=2[CH:15]=1.[NH2:16][C:17]1[CH:18]=[C:19]([CH:24]=[CH:25][CH:26]=1)[C:20]([O:22]C)=[O:21].N1C=CC=CC=1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10]([NH:16][C:17]3[CH:18]=[C:19]([CH:24]=[CH:25][CH:26]=3)[C:20]([OH:22])=[O:21])(=[O:12])=[O:11])=[C:7]([CH3:14])[C:6]=2[CH:15]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 78274Benzoic acid, 3-amino-, methyl esterHCID 27357565-Chloro-3-methylbenzo(b)thiophene-2-sulfonyl chloride

Product 1

HCID 569413063-{[(5-Chloro-3-methyl-1-benzothien-2-yl)sulfonyl]amino}benzoic acidYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5-chloro-3-methylbenzothiophene-2-sulfonyl chloride (200 mg, 0.711 mmol) in CH2Cl2 (5 mL) was added to a mixture of methyl 3-aminobenzoate (107 mg, 0.711 mmol) and pyridine (1 mL) in CH2Cl2 (5 mL). The reaction mixture was stirred at room temperature over night. The solvent was evaporated and the crude methyl 3-{[(5-chloro-3-methyl-1-benzothien-2-yl)sulfonyl]amino}benzoate (100 mg) was slurried in water (4 mL). LiOH (300 mg) was added and the mixture was stirred at room temperature for 2 h. The reaction was acidified by aqueous 2 M HCl and the white precipitate was collected by filtration, washed with CH2Cl2 (5 mL) and dried. The title compound was obtained in 28% yield (75 mg, over two steps). MS (ESI+) calcd for C16H12ClNO4S2 380.989627, found 380.989527.

Workup

  1. customThe solvent was evaporated
  2. additionLiOH (300 mg) was added
  3. stirringthe mixture was stirred at room temperature for 2 h
  4. filtrationthe white precipitate was collected by filtration
  5. washwashed with CH2Cl2 (5 mL)
  6. customdried

Sources & evidence

ORD record
ord-aedfd030ebc94b79bcb230e9aaf732f6
Source dataset
uspto-grants-2016_01
Patent number
US09233946B2

Reaction notes

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