Methylamine → HCID 57461305, compound

HRID 16612Notes

Reaction equation

HRID 16612 reaction equation
[C:1](N1C=CN=C1)([N:3]1C=CN=C1)=O.[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([S:22][C:23]2[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=2[C:25](O)=[O:26])=[CH:14]1.CN>C1COCC1>[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([S:22][C:23]2[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=2[C:25]([NH:3][CH3:1])=[O:26])=[CH:14]1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 107544492-(1H-indol-3-ylsulfanyl)benzoic Acid

Product 1

HCID 57461305HCID 57461305, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Carbonyldiimidazole (11 mmol) was added to a solution of 2-(1H-indol-3-ylsulfanyl)benzoic acid (Hamel, P.; Girard, M.; Tsou, N. N.; J. Heterocycl. Chem. 36, 1999, 643-652) (10 mmol) in dry THF (200 mL) and refluxed for 60 minutes under argon. Methyl amine (1M in THF; 40 ml) was added slowly to the reaction mixture and the mixture was stirred at room temperature for 16 hours. The mixture was evaporated in vacuo and the product purified by column chromatography on silica gel using ethyl acetate as an eluent.

Workup

  1. temperaturerefluxed for 60 minutes under argon
  2. customThe mixture was evaporated in vacuo
  3. customthe product purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-bf2d07f8753548edaed903db146b7451
Source dataset
uspto-grants-2010_06
Patent number
US07737170B2

Reaction notes

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