Water → Ethyl Z-2-(2-acetamidothiazol-4-yl)-2-butenoate

HRID 2231370Notes

Reaction equation

HRID 2231370 reaction equation
[C:1]([NH:4][C:5]([NH2:7])=[S:6])(=[O:3])[CH3:2].O.[CH:9](=[C:11]([C:17](=O)[CH2:18]Cl)[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH3:10]>CN(C)C=O>[C:1]([NH:4][C:5]1[S:6][CH:10]=[C:9](/[C:11](=[CH:17]/[CH3:18])/[C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:7]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 2723593AcetylthioureaHCID 54518096Ethyl 2-ethylidene-4-chloro-3-oxobutyrate

Product 1

HCID 13603194Ethyl Z-2-(2-acetamidothiazol-4-yl)-2-butenoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
15 °C

Procedure

14.6 parts by weight of acetylthiourea, 30 parts by volume of water and 50 parts by volume of N,N-dimethylformamide are heated up to 85° C. under nitrogen. 22.9 parts by weight of ethyl 2-ethylidene-4-chloro-3-oxobutyrate are then added at this temperature in the course of 40 minutes. The mixture is stirred at 80° to 85° C. for 1 hour and then cooled to 15° C., and, after 10 minutes, the precipitate which has separated out is filtered off with suction. The precipitate is suspended once in 34.5 parts by volume of water, filtered off with suction again and washed twice more with water. The crude product is dried and then extracted by stirring once in a mixture of 13.8 parts by volume of water and 41.8 parts by volume of ethanol for 10 minutes, filtered off with suction and rinsed with ethanol/water (3/1). After drying, 8.8 parts by weight of a pure product are obtained.

Workup

  1. waitafter 10 minutes
  2. customthe precipitate which has separated out
  3. filtrationis filtered off with suction
  4. filtrationfiltered off with suction again
  5. washwashed twice more with water
  6. dry with materialThe crude product is dried
  7. extractionextracted
  8. stirringby stirring once in a mixture of 13.8 parts by volume of water and 41.8 parts by volume of ethanol for 10 minutes
  9. filtrationfiltered off with suction
  10. washrinsed with ethanol/water (3/1)
  11. customAfter drying
  12. custom8.8 parts by weight of a pure product are obtained

Sources & evidence

ORD record
ord-da6a6ce211b54166a06580024a2f263c
Source dataset
uspto-grants-1988_11
Patent number
US04782162

Reaction notes

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