4-Phenoxyphenylthiourea → Isopropyl 5-methyl-4-{2-[(4-phenoxyphenyl)amino](1,3-thiazol-4-yl)}thiophene-2-carboxylate hydrobromide

HRID 2298666Notes

Reaction equation

HRID 2298666 reaction equation
[CH:1]([O:4][C:5]([C:7]1[S:8][C:9]([CH3:16])=[C:10]([C:12](=O)[CH2:13][Br:14])[CH:11]=1)=[O:6])([CH3:3])[CH3:2].[O:17]([C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:31]([NH2:33])=[S:32])=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[BrH:14].[CH3:16][C:9]1[S:8][C:7]([C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[O:6])=[CH:11][C:10]=1[C:12]1[N:33]=[C:31]([NH:30][C:27]2[CH:26]=[CH:25][C:24]([O:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[CH:29][CH:28]=2)[S:32][CH:13]=1

Participants

3

Reactant 2

HCID 27603494-PhenoxyphenylthioureaHCID 18537306Isopropyl 4-(2-bromoacetyl)-5-methylthiophene-2-carboxylate

Product 1

HCID 18536995Isopropyl 5-methyl-4-{2-[(4-phenoxyphenyl)amino](1,3-thiazol-4-yl)}thiophene-2-carboxylate hydrobromideYield 75%

Procedure

Isopropyl-4-(2-bromoacetyl)-5-methylthiophene-2-carboxylate (91 mg, 0.29 mmol) was allowed to react with 4-phenoxyphenylthiourea (72.6 mg) as described in Example 154, step (a) to give 115 mg (75% yield) of isopropyl 5-methyl-4-{2-[(4-phenoxyphenyl)amino](1,3-thiazol-4-yl)}thiophene-2-carboxylate hydrobromide. 1H NMR (DMSO-d6, 300 MHz) δ1.28 (d, 6H, J=6.2 Hz), 2.70 (s, 3H), 6.06 (quintet, 1H, J=6.2 Hz), 6.92-7.09 (m, 5H), 7.15 (s, 1H), 7.30-7.37 (m, 2H), 7.56-7.70 (m, 2H), 7.98 (s, 1H); Mass Spectrum (ESI) m/z calcd. for C24H22N2O3S2, 450.6 (M+H), found 451.2, 409.2 [—CH(CH3)2].

Sources & evidence

ORD record
ord-b553d459fe214bbea724bcfd0b26114e
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

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