Water → HCID 12831778, compound

HRID 2059052Notes

Reaction equation

HRID 2059052 reaction equation
Cl.[NH2:2][C:3]1[S:4][C:5]([CH2:10][CH3:11])=[C:6]([CH2:8][CH3:9])[N:7]=1.N1[CH:17]=[CH:16]C=CC=1.CC[C:20]([C:22](Cl)=[O:23])=[O:21].[OH2:25]>>[CH2:8]([C:6]1[N:7]=[C:3]([NH:2][C:20]([C:22]([O:23][CH2:16][CH3:17])=[O:25])=[O:21])[S:4][C:5]=1[CH2:10][CH3:11])[CH3:9]

Participants

5

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 11007880Butanoyl chloride, 2-oxo-HCID 12831772HCID 12831772, compound

Product 1

HCID 12831778HCID 12831778, compound

Procedure

2-Amino-4,5-diethylthiazole hydrochloride (2.9 g., 15 mmoles) was slurried in 20 ml. of pyridine and cooled in an ice-water bath. Ethyloxalyl chloride (2.3 g., 1.9 ml., 17 mmoles) was added dropwise over 10 minutes. The reaction was stirred for 15 minutes in the ice-water bath and then for 30 minutes at room temperature. The reaction mixture was diluted with approximately 70 ml. of ice and water and the oily precipitate which formed extracted into chloroform (2×75 ml.). The combined chloroform extracts were dried over anhydrous sodium sulfate, filtered and stripped in vacuo to an oil, which was crystallized by triturating and stirring with 40 ml. of water. Approximately 3 g. of crude product resulted. Recrystallization from approximately 30 ml. of cyclohexane gave purified ethyl 4,5-diethylthiazol-2-ylcarbamoylcarboxylate (1.8 g., m.p. 71.5°-72.5° C.).

Workup

  1. additionThe reaction mixture was diluted with approximately 70 ml
  2. extractionextracted into chloroform (2×75 ml.)
  3. dry with materialThe combined chloroform extracts were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customwas crystallized
  6. customby triturating
  7. customof crude product resulted
  8. customRecrystallization from approximately 30 ml
  9. customof cyclohexane gave
  10. custompurified ethyl 4,5-diethylthiazol-2-ylcarbamoylcarboxylate (1.8 g., m.p. 71.5°-72.5° C.)

Sources & evidence

ORD record
ord-f942cfa07b864458924a0b7f85659ef8
Source dataset
uspto-grants-1982_03
Patent number
US04321372

Reaction notes

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