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 1058478Notes

Reaction equation

HRID 1058478 reaction equation
[OH:1][C:2]1([C:18]([F:21])([F:20])[F:19])[CH2:6][S:5][C:4]([NH:7][C:8]2[CH:9]=[C:10]([C:14]([O:16][CH3:17])=O)[S:11][C:12]=2[CH3:13])=[N:3]1.NC(NC1C=C(C(OC)=S)SC=1C)=[S:24].BrCC(C(F)(F)F)=O>>[OH:1][C:2]1([C:18]([F:21])([F:20])[F:19])[CH2:6][S:5][C:4]([NH:7][C:8]2[CH:9]=[C:10]([C:14]([O:16][CH3:17])=[S:24])[S:11][C:12]=2[CH3:13])=[N:3]1

Participants

4

Reactant 3

HCID 790083-Bromo-1,1,1-trifluoro-2-propanoneHCID 18672216Methyl 4-{[4-hydroxy-4-(trifluoromethyl)(1,3-thiazolin-2-yl)]amino}-5-methylthiophene-2-carboxylateHCID 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

Methyl 4-{[4-hydroxy-4-(trifluoromethyl)(1,3-thiazolin-2-yl)]amino}-5-methylthiophene-2-carboxylate: 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-c4cf6a3db28840ad972c17e13e5aaf44
Source dataset
uspto-grants-2003_02
Patent number
US06515002B2

Reaction notes

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