2-Bromopropiophenone → [4-(4-Methyl-imidazol-1-yl)-phenyl]-(5-methyl-4-phenyl-thiazol-2-yl)-amine

HRID 604930Notes

Reaction equation

HRID 604930 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([NH2:16])=[S:15])=[CH:9][CH:8]=2)[CH:6]=1.Br[CH:18]([CH3:27])[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=O>>[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:8]=[CH:9][C:10]([NH:13][C:14]3[S:15][C:18]([CH3:27])=[C:19]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[N:16]=3)=[CH:11][CH:12]=2)[CH:6]=1

Participants

3

Reactant 2

HCID 164522-BromopropiophenoneHCID 86624711[4-(4-Methyl-imidazol-1-yl)-phenyl]-thiourea

Product 1

HCID 86624712[4-(4-Methyl-imidazol-1-yl)-phenyl]-(5-methyl-4-phenyl-thiazol-2-yl)-amineYield 94%

Procedure

Prepared in analogy to example 64d) from 100 mg (0.43 mmol) [4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea and 101 mg (0.47 mmol) 2-bromopropiophenone. 140 mg (94%) of the product was isolated as a colorless solid. MS ISP (m/e): 347.1 (100) (M+H)+. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=10.48 (s, 1H), 9.46 (s, 1H), 7.93 (s, 1H), 7.88 (d, 2H), 7.69 (d, 2H), 7.47 (t, 2H), 7.36 (t, 1H), 2.46 (s, 3H), 2.34 (s, 3H).

Sources & evidence

ORD record
ord-80ff2cd157a94f59a65fa6f8412a6d5a
Source dataset
uspto-grants-2011_03
Patent number
US07910740B2

Reaction notes

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