Water → Ethyl 2-(2-formamido-5-chlorothiazol-4-yl)-2-methoxyiminoacetate

HRID 568834Notes

Reaction equation

HRID 568834 reaction equation
[Cl:1]N1C(=O)N(Cl)C(=O)N(Cl)C1=O.[CH:13]([NH:15][C:16]1[S:17][CH:18]=[C:19]([C:21](=[N:27][O:28][CH3:29])[C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:20]=1)=[O:14].O>CN(C)C=O>[CH:13]([NH:15][C:16]1[S:17][C:18]([Cl:1])=[C:19]([C:21](=[N:27][O:28][CH3:29])[C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:20]=1)=[O:14]

Participants

5

Reactant 3

HCID 962WaterHCID 6909Trichloroisocyanuric AcidHCID 53737196Ethyl 2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetate

Product 1

HCID 54156297Ethyl 2-(2-formamido-5-chlorothiazol-4-yl)-2-methoxyiminoacetateYield 224.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Trichloroisocyanuric acid (6.7 g.) was added portionwise to a chilled solution of ethyl 2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetate (syn isomer, 20.0 g.) in dry dimethylformamide (400 ml.) and stirred at room temperature for 2 hrs. The reaction mixture was poured into chilled water (2 l.), and the precipitates were collected by filtration, washed with water and dried to give ethyl 2-(2-formamido-5-chlorothiazol-4-yl)-2-methoxyiminoacetate (syn isomer, 18.9 g.).

Workup

  1. additionThe reaction mixture was poured
  2. filtrationthe precipitates were collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-fee01d36f4424306987ecc3074957a7e
Source dataset
uspto-grants-1988_03
Patent number
US04729991

Reaction notes

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