Thiourea → Isopropyl 4-(2-amino(1,3-thiazol-4-yl))-5-methylthiophene-2-carboxylate

HRID 2298635Notes

Reaction equation

HRID 2298635 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:6]=[C:7]([C:11]([O:13][CH:14]([CH3:16])[CH3:15])=[O:12])[S:8][C:9]=1[CH3:10])=O.[NH2:17][C:18]([NH2:20])=[S:19]>>[NH2:20][C:18]1[S:19][CH:2]=[C:3]([C:5]2[CH:6]=[C:7]([C:11]([O:13][CH:14]([CH3:16])[CH3:15])=[O:12])[S:8][C:9]=2[CH3:10])[N:17]=1

Participants

3

Reactant 2

HCID 2723790ThioureaHCID 18537306Isopropyl 4-(2-bromoacetyl)-5-methylthiophene-2-carboxylate

Product 1

HCID 18536917Isopropyl 4-(2-amino(1,3-thiazol-4-yl))-5-methylthiophene-2-carboxylateYield 107.1%

Procedure

A solution of 260 mg (0.85 mmol) of isopropyl 4-(2-bromoacetyl)-5-methylthiophene-2-carboxylate was reacted with 65 mg (0.85 mmol) of thiourea in a manner similar to Example 8, step (a) to give isopropyl 4-(2-amino(1,3-thiazol-4-yl))-5-methylthiophene-2-carboxylate (257 mg, quantitive yield) as a white solid. 1H-NMR (DMSO-d6; 300 MHz) δ7.90 (s, 1H), 6.93 (s, 1H), 5.09 (septet, 1H, J=6.2 Hz), 2.61 (s, 3H), 1.29 (d, 6H, J=6.2 Hz). Mass spectrum (ESI, m/z): Calcd. for C12H14N2O2S2 283.1 (M+H), found 283.1

Sources & evidence

ORD record
ord-08a124dc255943bbb34f104e3816d056
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

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