Acetic Anhydride → Ethyl 2-formamidothiazol-4-acetate

HRID 638432

Reaction equation

HRID 638432 reaction equation
[C:1](OC(=O)C)(=[O:3])C.[NH2:8][C:9]1[S:10][CH:11]=[C:12]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:13]=1>C(O)=O>[CH:1]([NH:8][C:9]1[S:10][CH:11]=[C:12]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:13]=1)=[O:3]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 1044544-Thiazoleacetic acid, 2-amino-, ethyl esterHCID 178470764HCID 178470764, compound

Product 1

HCID 688091Ethyl 2-formamidothiazol-4-acetate

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To acetic anhydride (384 ml.) was dropwise added formic acid (169.2 ml.) over 15 to 20 minutes under cooling below 35° C., and the mixture was stirred for 1 hour at 55° to 60° C. To the mixture was added ethyl 2-(2-amino-1,3-thiazol-4-yl)-acetate, which can be represented as ethyl 2-(2-imino-2,3-dihydro-1,3-thiazol-4-yl)acetate, (506 g.) over 15 to 20 minutes under ice-cooling and stirring, and then the mixture was stirred for 1 hour at room temperature. After the reaction, the solvents were distilled off. To the residue was added diisopropyl ether (2500 ml.), and the mixture was stirred for 1 hour at room temperature. The precipitates were collected by filtration, washed with diisopropyl ether and then dried to give ethyl 2-(2-formylamino-1,3-thiazol-4-yl)acetate, which can be represented as ethyl 2-(2-formylimino-2,3-dihydro-1,3-thiazol-4yl)acetate, (451.6 g.), mp. 125° to 126° C. The remaining filtrate was concentrated, and the residue was washed with diisopropyl ether (500 ml.) and then dried to give further the same object compound (78.5 g.).

Workup

  1. customover 15 to 20 minutes
  2. temperatureunder cooling below 35° C.
  3. temperaturecooling
  4. stirringstirring
  5. stirringthe mixture was stirred for 1 hour at room temperature
  6. customAfter the reaction
  7. distillationthe solvents were distilled off
  8. additionTo the residue was added diisopropyl ether (2500 ml.)
  9. stirringthe mixture was stirred for 1 hour at room temperature
  10. filtrationThe precipitates were collected by filtration
  11. washwashed with diisopropyl ether
  12. customdried

Sources & evidence

ORD record
ord-998db0259b1b4104983455e18b72dbde
Source dataset
uspto-grants-1985_12
Patent number
US04560765

Linked notes

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