Phenacyl bromide → Methyl 5-methyl-4-(4-phenyl(1,3-thiazol-2-yl))thiophene-2-carboxylate

HRID 2298630Notes

Reaction equation

HRID 2298630 reaction equation
[NH2:1][C:2](=[S:13])[C:3]1[CH:4]=[C:5]([C:9]([O:11][CH3:12])=[O:10])[S:6][C:7]=1[CH3:8].Br[CH2:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=O>>[CH3:8][C:7]1[S:6][C:5]([C:9]([O:11][CH3:12])=[O:10])=[CH:4][C:3]=1[C:2]1[S:13][CH:15]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:1]=1

Participants

3

Reactant 2

HCID 6259Phenacyl bromideHCID 18537096Methyl 4-(aminothioxomethyl)-5-methylthiophene-2-carboxylate

Product 1

HCID 18536825Methyl 5-methyl-4-(4-phenyl(1,3-thiazol-2-yl))thiophene-2-carboxylate

Procedure

A solution of 200 mg (0.93 mmol) of methyl 4-(aminothioxomethyl)-5-methylthiophene-2-carboxylate was reacted with 185 mg (0.93 mmol) of 2-bromoacetophenone in a manner similar to Example 8, step (a) to give, after purification by preparative thin layer chromatography eluting with hexanes:ethyl acetate 7/3 (v:v), a mixture of methyl 5-methyl-4-(4-phenyl(1,3-thiazol-2-yl))thiophene-2-carboxylate and methyl 4-cyano-5-methylthiophene-2-carboxylate (96 mg, 36%) as a solid.

Workup

  1. customto give
  2. customafter purification by preparative thin layer chromatography
  3. washeluting with hexanes
  4. additionethyl acetate 7/3 (v:v), a mixture of methyl 5-methyl-4-(4-phenyl(1,3-thiazol-2-yl))thiophene-2-carboxylate and methyl 4-cyano-5-methylthiophene-2-carboxylate (96 mg, 36%) as a solid

Sources & evidence

ORD record
ord-0b3daf0446e8408ba5b94533e4ab34a1
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

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