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

HRID 2298667Notes

Reaction equation

HRID 2298667 reaction equation
[Br:1][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.[C:17]1([NH:23][C:24]([NH2:26])=[S:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[BrH:1].[CH3:10][C:9]1[S:8][C:7]([C:11]([O:13][CH:14]([CH3:16])[CH3:15])=[O:12])=[CH:6][C:5]=1[C:3]1[N:26]=[C:24]([NH:23][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[S:25][CH:2]=1

Participants

3

Reactant 2

HCID 676454PhenylthioureaHCID 18537306Isopropyl 4-(2-bromoacetyl)-5-methylthiophene-2-carboxylate

Product 1

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

Procedure

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-82f78056dbf3499ba5893988e2f88513
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

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