2-(2-Methoxy-5-morpholin-4-yl-phenylamino)-2-thioxo-acetamide → 4-Methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid amide

HRID 1358233Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:5][C:4]=1[NH:15][C:16](=[S:20])[C:17]([NH2:19])=[O:18]>O.[Fe-3](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+]>[CH3:1][O:2][C:3]1[C:4]2[N:15]=[C:16]([C:17]([NH2:19])=[O:18])[S:20][C:5]=2[C:6]([N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A suspension of 220 mg (0.75 mmol) 2-(2-methoxy-5-morpholin-4-yl-phenylamino)-2-thioxo-acetamide in 2.88 ml 1N aqueous sodiumhydroxde was added to a solution of 813 mg (2.47 mmol) potassium ferricyanide in 2 ml water. The mixture was stirred at 50° C. for 30 minutes and then at room temperature overnight. The precipitate was separated by filtration, dissolved in dichloromethane and purified by column chromatography on silicagel with ethyl acetate/hexane 1/1. 4-methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid amide, 32 mg (15%), was obtained as yellow crystals with mp.: 228-230° C., MS m/e (%): 294 (M+H+, 100).

Workup

customat room temperature
customovernight
customThe precipitate was separated by filtration
dissolutiondissolved in dichloromethane
custompurified by column chromatography on silicagel with ethyl acetate/hexane 1/1

Sources & evidence

ORD record: ord-ed6cafa0947f4a07b092289bf97913bd
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06596718B1

Reaction notes

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