Bromine → methyl N-[5-bromo-4-(4-bromophenyl)-thiazol-2-yl]-N-methylaminoacetate

HRID 36014Notes

Reaction equation

HRID 36014 reaction equation
[Br:1]Br.[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([N:15]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH3:16])[S:13][CH:14]=2)=[CH:6][CH:5]=1.C([O-])(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(O)(=O)C>[Br:1][C:14]1[S:13][C:12]([N:15]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH3:16])=[N:11][C:10]=1[C:7]1[CH:6]=[CH:5][C:4]([Br:3])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 14748493methyl N-[4-(4-bromophenyl)-2-thiazolyl]-N-methylamino-acetate

Product 1

HCID 14748503methyl N-[5-bromo-4-(4-bromophenyl)-thiazol-2-yl]-N-methylaminoacetateYield 98.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of 2.34 g (0.015 mol) of bromine in 5 ml of glacial acetic acid is added dropwise with stirring in the course of 45 minutes at room temperature to a mixture of 4.5 g (0.013 mol) of methyl N-[4-(4-bromophenyl)-thiazol-2-yl]-N-methylaminoacetate and 2.5 g (0.03 mol) of sodium acetate in 30 ml of glacial acetic acid, the mixture is subsequently stirred with an excess of aqueous saturated sodium hydrogen carbonate solution, and the precipitate which has separated out is filtered off with suction. After drying, 5.4 g (97% of theory) of methyl N-[5-bromo-4-(4-bromophenyl)-thiazol-2-yl]-N-methylaminoacetate are obtained as an oil.

Workup

  1. customthe precipitate which has separated out
  2. filtrationis filtered off with suction
  3. customAfter drying

Sources & evidence

ORD record
ord-90e2223e5fba4ba4adbabd3233aeceaa
Source dataset
uspto-grants-1995_05
Patent number
US05412100

Reaction notes

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