3-Bromo-1,1,1-trifluoro-2-propanone → Methyl 4-{[4-hydroxy-4-(trifluoromethyl)(1,3-thiazolin-2-yl)]amino}-5-methylthiothiophene-2-carboxylate

HRID 2298670Notes

Reaction equation

HRID 2298670 reaction equation
[NH2:1][C:2]([NH:4][C:5]1[CH:6]=[C:7]([C:11]([O:13][CH3:14])=[S:12])[S:8][C:9]=1[CH3:10])=[S:3].Br[CH2:16][C:17]([C:19]([F:22])([F:21])[F:20])=[O:18]>>[OH:18][C:17]1([C:19]([F:22])([F:21])[F:20])[CH2:16][S:3][C:2]([NH:4][C:5]2[CH:6]=[C:7]([C:11]([O:13][CH3:14])=[S:12])[S:8][C:9]=2[CH3:10])=[N:1]1

Participants

3

Reactant 2

HCID 790083-Bromo-1,1,1-trifluoro-2-propanoneHCID 86583851Methyl 4-[(aminothioxomethyl)amino]-5-methylthiothiophene-2-carboxylate

Product 1

HCID 131723714Methyl 4-{[4-hydroxy-4-(trifluoromethyl)(1,3-thiazolin-2-yl)]amino}-5-methylthiothiophene-2-carboxylateYield 54%

Procedure

Using a procedure similar to Example 204, step (a), 56 mg (0.21 mmol) of methyl 4-[(aminothioxomethyl)amino]-5-methylthiothiophene-2-carboxylate was allowed to react with 40 mg (0.21 mmol) of bromotrifluoroacetone (Aldrich Chemical Co., Milwaukee, Wis.) to afford 40.3 mg (54%) of methyl 4-{[4-hydroxy-4-(trifluoromethyl)(1,3-thiazolin-2-yl)]amino}-5-methylthiothiophene-2-carboxylate. Mass spectrum (ESI, m/z): Calcd. for C11H11F3N2O3S3, 373.00 (M+H), found 373.0.

Sources & evidence

ORD record
ord-f24e444322304d76a69e2fc8e81ec2b3
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

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