Benzoic acid, 3-amino-, methyl ester → HCID 66799823, compound

HRID 589718Notes

Reaction equation

HRID 589718 reaction equation
[Br: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][CH3:23])=[O:21]>C(Cl)Cl>[CH3:23][O:22][C:20](=[O:21])[C:19]1[CH:24]=[CH:25][CH:26]=[C:17]([NH:16][S:10]([C:8]2[S:9][C:5]3[CH:4]=[CH:3][C:2]([Br:1])=[CH:15][C:6]=3[C:7]=2[CH3:14])(=[O:12])=[O:11])[CH:18]=1

Participants

4

Reactant 2

HCID 78274Benzoic acid, 3-amino-, methyl esterHCID 27355915-bromo-3-methyl-1-benzothiophene-2-sulfonyl chloride2×

Product 1

HCID 66799823HCID 66799823, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The intermediate methyl 3-{[(5-bromo-3-methyl-1-benzothiophen-2-yl)sulfonyl]amino}benzoate was prepared according to General Procedure 1, described in Example 1, starting from 5-bromo-3-methylbenzothiophene-2-sulfonyl chloride (Intermediate 10) (870 mg, 2.67 mmol) and methyl 3-aminobenzoate (367 mg, 2.43 mmol). The reaction mixture was diluted with CH2Cl2 (20 mL) and washed with 1M HCl (30 mL). The organic phase was dried (Na2SO4). Evaporation of the solvents afforded 600 mg of crude methyl-3-{[(5-bromo-3-methyl-1-benzothien-2-yl)sulfonyl]amino}benzoate, which was used without further purification.

Workup

  1. customThe intermediate methyl 3-{[(5-bromo-3-methyl-1-benzothiophen-2-yl)sulfonyl]amino}benzoate was prepared
  2. washwashed with 1M HCl (30 mL)
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. customEvaporation of the solvents

Sources & evidence

ORD record
ord-70a222c4d1154116aa5318cbf0f1b375
Source dataset
uspto-grants-2016_01
Patent number
US09233946B2

Reaction notes

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