Acetic Anhydride → HCID 53857836, compound

HRID 256425Notes

Reaction equation

HRID 256425 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH3:14])=[C:5]([C:7](=[N:11][O:12][CH3:13])[C:8]([OH:10])=[O:9])[N:6]=1.[C:15](OC(=O)C)(=[O:17])C>C(O)=O>[CH:15]([NH:1][C:2]1[S:3][C:4]([CH3:14])=[C:5]([C:7](=[N:11][O:12][CH3:13])[C:8]([OH:10])=[O:9])[N:6]=1)=[O:17]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 54403172HCID 54403172, compound

Product 1

HCID 53857836HCID 53857836, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of 2-(2-amino-5-methylthiazol-4-yl)-2-methoxyiminoacetic acid (syn isomer, 2.6 g.), acetic anhydride (31 ml.) and formic acid (13 ml.) was stirred at room temperature for 2 hrs. and then evaporated in vacuo. The residue was dissolved in a mixture of water and ethyl acetate. The ethyl acetate layer was separated, washed with an aqueous solution of sodium chloride, dried over magnesium sulfate, treated with activated charcoal and then filtered. The filtrate was evaporated in vacuo. The oily residue was treated with n-hexane and diisopropyl ether, and the precipitates were collected by filtration to give 2-(2-formamido-5-methylthiazol-4-yl)-2-methoxyiminoacetic acid (syn isomer, 2.8 g.).

Workup

  1. customand then evaporated in vacuo
  2. dissolutionThe residue was dissolved in a mixture of water and ethyl acetate
  3. customThe ethyl acetate layer was separated
  4. washwashed with an aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. additiontreated with activated charcoal
  7. filtrationfiltered
  8. customThe filtrate was evaporated in vacuo
  9. additionThe oily residue was treated with n-hexane and diisopropyl ether
  10. filtrationthe precipitates were collected by filtration

Sources & evidence

ORD record
ord-cc96c4eee48a4475ae742180152286ca
Source dataset
uspto-grants-1987_10
Patent number
US04703046

Reaction notes

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