Phenylthiourea → Isopropyl 5-methyl-4-[2-(phenylamino)(1,3-thiazol-4-yl)]-thiophene-2-carboxylate hydrobromide

HRID 2186623Notes

Reaction equation

HRID 2186623 reaction equation
Br.S1C=CC=C1C(O)=O.[Br:10][CH2:11][C:12]([C:14]1[CH:15]=[C:16]([C:20]([O:22][CH:23]([CH3:25])[CH3:24])=[O:21])[S:17][C:18]=1[CH3:19])=O.[C:26]1([NH:32][C:33]([NH2:35])=[S:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[BrH:10].[CH3:19][C:18]1[S:17][C:16]([C:20]([O:22][CH:23]([CH3:25])[CH3:24])=[O:21])=[CH:15][C:14]=1[C:12]1[N:35]=[C:33]([NH:32][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[S:34][CH:11]=1

Participants

4

Reactant 3

HCID 676454PhenylthioureaHCID 18537306Isopropyl 4-(2-bromoacetyl)-5-methylthiophene-2-carboxylateHCID 86758185Thiophene-2-carboxylate hydrobromide

Product 1

HCID 18537295Isopropyl 5-methyl-4-[2-(phenylamino)(1,3-thiazol-4-yl)]-thiophene-2-carboxylate hydrobromideYield 87%

Procedure

Isopropyl 5-methyl-4-[2-phenylamino)(1,3-thiazol-4-yl)]-thiophene-2-carboxylate hydrobromide: Isopropyl 4-(2-bromoacetyl)-5-methylthiophene-2-carboxylate (64 mg, 0.21 mmol) was allowed to react with phenylthiourea (32.1 mg) as described in Example 154, step (a) to give 80 mg (87% yield) of isopropyl 5-methyl-4-[2-(phenylamino)(1,3-thiazol-4-yl)]-thiophene-2-carboxylate hydrobromide. Mass Spectrum (ESI) m/z calcd. for C18H18N2O2S2, 358.5 (M+H), found 359.2.

Sources & evidence

ORD record
ord-c7dc991ab51441a69e777b60068f4ca0
Source dataset
uspto-grants-2002_06
Patent number
US06403633B2

Reaction notes

Loading…