N-bromobutanimide → 4-(2',4'-Dichlorophenyl)-5-bromomethyl thiazole

HRID 1729273Notes

Reaction equation

HRID 1729273 reaction equation
Br.[Cl:2][C:3]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:4]=1[C:10]1[N:11]=[CH:12][S:13][C:14]=1[CH3:15].[Br:16]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Cl:2][C:3]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:4]=1[C:10]1[N:11]=[CH:12][S:13][C:14]=1[CH2:15][Br:16]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 190124704-(2',4'-Dichlorophenyl)-5-methylthiazole hydrobromide

Product 1

HCID 190124684-(2',4'-Dichlorophenyl)-5-bromomethyl thiazole

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

The product was neutralised and the free thiazole was treated with N-bromosuccinimide in refluxing carbon tetrachloride for 16 hours with irradiation by a lamp to give 4-(2',4'-dichlorophenyl)-5-bromomethyl thiazole The crude product was dissolved in dry acetonitrile, sodium triazole (0.91 g; 0.01 mole) was added and the mixture stirred for 16 hours at 20° C. to give, after chromatography using silica gel/chloroform: 2% ethanol, the title compound (0.71 g; 23%). m.p. 120°-123° C.

Workup

  1. customwith irradiation by a lamp

Sources & evidence

ORD record
ord-1e890ddce1dd460591518f7d5749c05a
Source dataset
uspto-grants-1994_07
Patent number
US05332753

Reaction notes

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