Benzoyl Peroxide → Ethyl 2-(2-formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetate

HRID 568836Notes

Reaction equation

HRID 568836 reaction equation
C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[CH:19]([NH:21][C:22]1[S:23][CH:24]=[C:25]([C:27](=[N:33][O:34][CH3:35])[C:28]([O:30][CH2:31][CH3:32])=[O:29])[N:26]=1)=[O:20].[Br:36]N1C(=O)CCC1=O>C1C=CC=CC=1>[CH:19]([NH:21][C:22]1[S:23][C:24]([Br:36])=[C:25]([C:27](=[N:33][O:34][CH3:35])[C:28]([O:30][CH2:31][CH3:32])=[O:29])[N:26]=1)=[O:20]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 53737196Ethyl 2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetate

Product 1

HCID 53894989Ethyl 2-(2-formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetateYield 94.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A small amount of benzoyl peroxide was added to a suspension of ethyl 2(2-formamidothiazol-4-yl)-2-methoxyiminoacetate (syn isomer, 7.55 g.) and N-bromosuccinimide (5.75 g.) in dry benzene (150 ml.) and refluxed under heating for an hour. After cooling, the reaction mixture was washed with water three times, dried over magnesium sulfate, treated with activated charcoal and then evaporated in vacuo. The residue was pulverized with n-hexane, and the precipitates were collected by filtration, washed with n-hexane and water successively and dried to give ethyl 2-(2-formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetate (syn isomer, 9.3 g.).

Workup

  1. temperaturerefluxed
  2. temperatureunder heating for an hour
  3. temperatureAfter cooling
  4. washthe reaction mixture was washed with water three times
  5. dry with materialdried over magnesium sulfate
  6. additiontreated with activated charcoal
  7. customevaporated in vacuo
  8. filtrationthe precipitates were collected by filtration
  9. washwashed with n-hexane and water successively
  10. customdried

Sources & evidence

ORD record
ord-92a1c6d0c83a42498cc3554908449f1e
Source dataset
uspto-grants-1988_03
Patent number
US04729991

Reaction notes

Loading…