(2-Formamido-1,3-thiazol-4-yl)(oxo)acetic acid → HCID 53828491, compound

HRID 745703Notes

Reaction equation

HRID 745703 reaction equation
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=O)[C:10]([OH:12])=[O:11])[N:8]=1)=[O:2].[OH:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=1[NH:22][C:23](=[O:27])[CH2:24][O:25][NH2:26]>C(O)C>[OH:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=1[NH:22][C:23]([CH2:24][O:25][N:26]=[C:9]([C:7]1[N:8]=[C:4]([NH:3][CH:1]=[O:2])[S:5][CH:6]=1)[C:10]([OH:12])=[O:11])=[O:27]

Participants

4

Reactant 2

HCID 13116693(2-Formamido-1,3-thiazol-4-yl)(oxo)acetic acidHCID 21286870HCID 21286870, compound

Product 1

HCID 53828491HCID 53828491, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-(2-formamidothiazol-4-yl)glyoxylic acid (2.79 g.) and N-(2-hydroxy-5-chlorophenyl)-2-(aminooxy)-acetamide (3.32 g.) in ethanol (30 ml.) was stirred for 5 hours at room temperature. The reaction mixture was evaporated to dryness and to the residue was added a mixture of ethyl acetate, water and 10% hydrochloric acid followed by stirring. The ethyl acetate layer was separated, washed with diluted hydrochloric acid and an aqueous solution of sodium chloride, dried over magnesium sulfate, concentrated to a small volume and allowed to stand under ice-cooling. The resulting precipitates were collected by filtration, washed with ethyl acetate and then dried under reduced pressure to give the title compound (4.59 g.).

Workup

  1. customThe reaction mixture was evaporated to dryness and to the residue
  2. additionwas added
  3. additiona mixture of ethyl acetate, water and 10% hydrochloric acid
  4. stirringby stirring
  5. customThe ethyl acetate layer was separated
  6. washwashed with diluted hydrochloric acid
  7. dry with materialan aqueous solution of sodium chloride, dried over magnesium sulfate
  8. concentrationconcentrated to a small volume
  9. temperaturecooling
  10. customThe resulting precipitates
  11. filtrationwere collected by filtration
  12. washwashed with ethyl acetate
  13. customdried under reduced pressure

Sources & evidence

ORD record
ord-f6de25b57f1d42599b603f11d8210258
Source dataset
uspto-grants-1986_07
Patent number
US04599426

Reaction notes

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