Formic Acid → HCID 20254335, compound

HRID 1659405Notes

Reaction equation

HRID 1659405 reaction equation
[C:1](OC(=O)C)(=[O:3])C.O.[OH:9][CH:10]([C:14]1[S:18][C:17]([NH2:19])=[N:16][CH:15]=1)[C:11]([OH:13])=[O:12].[CH:20](O)=[O:21]>>[CH:1]([O:9][CH:10]([C:14]1[S:18][C:17]([NH:19][CH:20]=[O:21])=[N:16][CH:15]=1)[C:11]([OH:13])=[O:12])=[O:3]

Participants

5

Reactant 4

HCID 284Formic Acid2×HCID 7918Acetic Anhydride2×HCID 70491261HCID 70491261, compoundHCID 178509089HCID 178509089, compound

Product 1

HCID 20254335HCID 20254335, compound

Procedure

A mixture of formic acid (10 m mol) and acetic anhydride (10 m mol) was stirred for 2 hours at 50° to 60° C. and then cooled to -7° to -5° C. To the mixture was added 2-hydroxy-2-(2-amino-1,3-thiazol-5-yl)acetic acid hydrate, which can be represented as 2-hydroxy-2-(2-imino-2,3-dihydro-1,3-thiazol-5-yl)acetic acid hydrate, (0.48 g.) at the same temperature, and the mixture was stirred for 3 hours at the same temperature. To the mixture was further added a mixture of formic acid (2.5 m mol) and acetic anhydride (2.5 m mol) at the same temperature and then the mixture was further stirred for 1 hour at the same temperature. After the reaction, the solvent was distilled off. To the residue were added water and methyl isobutyl ketone and then the insoluble material was filtered off. The filtrate was treated with an activated charcoal, and the methyl isobutyl ketone layer was separated. The remaining aqueous layer was further extracted with methyl isobutyl ketone. The methyl isobutyl ketone layers were combined together, dried over magnesium sulfate, treated with an activated charcoal, and then the solvent was distilled off. The residue was pulverized in diethyl ether to give powder of 2-formyloxy-2-(2-formylamino-1,3-thiazol-5-yl)acetic acid, which can be represented as 2-formyloxy-2-(2-formylimino-2,3-dihydro-1,3-thiazol-5-yl)acetic acid, (0.31 g.).

Workup

  1. temperaturecooled to -7° to -5° C
  2. stirringthe mixture was stirred for 3 hours at the same temperature
  3. additionTo the mixture was further added
  4. stirringthe mixture was further stirred for 1 hour at the same temperature
  5. customAfter the reaction
  6. distillationthe solvent was distilled off
  7. additionTo the residue were added water and methyl isobutyl ketone
  8. filtrationthe insoluble material was filtered off
  9. additionThe filtrate was treated with an activated charcoal
  10. customthe methyl isobutyl ketone layer was separated
  11. extractionThe remaining aqueous layer was further extracted with methyl isobutyl ketone
  12. dry with materialdried over magnesium sulfate
  13. additiontreated with an activated charcoal
  14. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-ff28e706e9974ee2b13dd7b5cb2f00ba
Source dataset
uspto-grants-1981_12
Patent number
US04303655

Reaction notes

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