Phenacyl bromide → HCID 18537476, compound

HRID 2298634Notes

Reaction equation

HRID 2298634 reaction equation
[NH2:1][C:2](=[S:15])[C:3]1[CH:4]=[C:5]([C:9]([O:11][CH:12]([CH3:14])[CH3:13])=[O:10])[S:6][C:7]=1[CH3:8].Br[CH2:17][C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=O>>[CH3:8][C:7]1[S:6][C:5]([C:9]([O:11][CH:12]([CH3:13])[CH3:14])=[O:10])=[CH:4][C:3]=1[C:2]1[S:15][CH:17]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:1]=1

Participants

3

Reactant 2

HCID 6259Phenacyl bromideHCID 18537366HCID 18537366, compound

Product 1

HCID 18537476HCID 18537476, compound

Procedure

A solution of 375 mg (1.54 mmol) of isopropyl 4-(aminothioxomethyl)-5-methylthiophene-2-carboxylate was reacted with 307 mg (1.54 mmol) of 2-bromoacetophenone (Aldrich, Milwaukee, Wis., USA) in a manner similar to Example 8, step (a) to give, after crystallization from methanol, isopropyl 5-methyl-4-(4-phenyl(1,3-thiazol-2-yl))thiophene-2-carboxylate (347 mg, 66%) as light brown needles. 1H-NMR (DMSO-d6; 300 MHz) δ8.23 (s, 1H), 8.09 (s, 1H), 8.05 (m, 2H), 7.49 (m, 2H), 7.38 (m, 1H), 5.13 (septet, 1H, J=6.2 Hz), 2.86 (s, 3H), 1.33 (d, 6H, J=6.2 Hz). Mass spectrum (ESI, m/z): Calcd. for C18H17NO2S2 344.1 (M+H), found 344.1.

Workup

  1. customto give
  2. customafter crystallization from methanol, isopropyl 5-methyl-4-(4-phenyl(1,3-thiazol-2-yl))thiophene-2-carboxylate (347 mg, 66%) as light brown needles

Sources & evidence

ORD record
ord-d88f199dbb314c1e9028121afa302216
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

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