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

HRID 256428Notes

Reaction equation

HRID 256428 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-df865b00498d439f8c18d962cbf85c64
Source dataset
uspto-grants-1987_10
Patent number
US04703046

Reaction notes

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