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

HRID 2298638Notes

Reaction equation

C([C:3]1([CH2:17][CH3:18])[S:7][CH:6]([C:8]([O:10][CH:11]([CH3:13])[CH3:12])=[O:9])[CH:5]=[C:4]1[C:14]([NH2:16])=[S:15])C.Br[CH2:20][C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=O>>[CH2:17]([C:3]1[S:7][C:6]([C:8]([O:10][CH:11]([CH3:12])[CH3:13])=[O:9])=[CH:5][C:4]=1[C:14]1[S:15][CH:20]=[C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:16]=1)[CH3:18]

Participants

Reactant 2

HCID 6259Phenacyl bromide

HCID 18536974Isopropyl 5-ethyl-4-(aminothioxomethyl)-5-ethylthiophene-2-carboxylate

Product 1

HCID 18537061Isopropyl 5-ethyl-4-(4-phenyl(1,3-thiazol-2-yl))thiophene-2-carboxylateYield 49%

Procedure

A solution of 450 mg (1.75 mmol) of isopropyl 5-ethyl-4-(aminothioxomethyl)-5-ethylthiophene-2-carboxylate was reacted with 348 mg (1.75 mmol) of 2-bromoacetophenone (Aldrich, Milaukee, Wis., USA) in a manner similar to Example 8, step (a) to give isopropyl 5-ethyl-4-(4-phenyl(1,3-thiazol-2-yl))thiophene-2-carboxylate (303 mg, 49%) as an off-white solid. 1H-NMR (DMSO-d6; 300 MHz) δ8.22 (s, 1H), 8.07 (s, 1H), 8.03 (m, 2H), 7.49 (m, 2H), 7.38 (m, 1H), 5.13 (septet, 1H, J=6.2 Hz), 3.34 (q, 2H, J=7.4 Hz), 1.39 (t, 3H, J=7.4 Hz), 1.33 (d, 6H, J=6.2 Hz). Mass spectrum (ESI, m/z): Calcd. for C19H19NO2S2 358.1 (M+H), found 358.1.

Sources & evidence

ORD record: ord-bb1cf394f56c476fa8dc3f686f22b44d
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492403B1

Reaction notes

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