Formic Acid → HCID 53939076, compound

HRID 255735Notes

Reaction equation

HRID 255735 reaction equation
[C:1](OC(=O)C)(=[O:3])C.C(O)=O.[NH2:11][C:12]1[S:13][CH:14]=[C:15]([C:17](=[N:23][O:24][CH2:25][CH2:26][Br:27])[C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:16]=1>O>[CH:1]([NH:11][C:12]1[S:13][CH:14]=[C:15]([C:17](=[N:23][O:24][CH2:25][CH2:26][Br:27])[C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:16]=1)=[O:3]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 54560759HCID 54560759, compound

Product 1

HCID 53939076HCID 53939076, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of acetic anhydride (15.9 g.) and formic acid (7.15 g.) was stirred at 50° C. for an hour. After cooling, ethyl 2-(2-aminothiazol-4-yl)-2-(2-bromoethoxyimino)acetate (syn isomer, 25 g.) was added to the solution and stirred at room temperature for an hour. The resultant solution was poured into water and extracted with ethyl acetate twice. The extracts were washed with a saturated aqueous solution of sodium chloride, a saturated aqueous solution of sodium bicarbonate (three times) and a saturated aqueous solution of sodium chloride in turn, and dried over magnesium sulfate. After concentrating the solution in vacuo, the oily residue was triturated with a mixture of diisopropyl ether and diethyl ether. The precipitates were collected by filtration to give ethyl 2-(2-formamidothiazol-4-yl)-2-(2-bromoethoxyimino)acetate (syn isomer, 16.75 g.), mp. 95° to 98° C.

Workup

  1. temperatureAfter cooling
  2. stirringstirred at room temperature for an hour
  3. extractionextracted with ethyl acetate twice
  4. washThe extracts were washed with a saturated aqueous solution of sodium chloride
  5. dry with materiala saturated aqueous solution of sodium bicarbonate (three times) and a saturated aqueous solution of sodium chloride in turn, and dried over magnesium sulfate
  6. concentrationAfter concentrating the solution in vacuo
  7. customthe oily residue was triturated with a mixture of diisopropyl ether and diethyl ether
  8. filtrationThe precipitates were collected by filtration

Sources & evidence

ORD record
ord-65e1eca9c2b64bbaba8088992a376882
Source dataset
uspto-grants-1987_10
Patent number
US04698337

Reaction notes

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