Water → HCID 53930828, compound

HRID 275351Notes

Reaction equation

HRID 275351 reaction equation
[CH3:1][O:2][CH2:3][C:4]([NH2:6])=[S:5].[CH2:7]([O:9][C:10](=[O:16])[CH:11](Cl)[C:12]([CH3:14])=O)[CH3:8].O>C1C=CC=CC=1.C(OCC)(=O)C>[CH2:7]([O:9][C:10]([C:11]1[S:5][C:4]([CH2:3][O:2][CH3:1])=[N:6][C:12]=1[CH3:14])=[O:16])[CH3:8]

Participants

6

Reactant 3

HCID 962WaterHCID 11858Ethyl 2-chloroacetoacetateHCID 203233692-Methoxyethanethioamide

Product 1

HCID 53930828HCID 53930828, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

20 g of methoxythioacetamide are added, with vigorous stirring, to 31.3 g of 2-chloroacetoacetic acid ethyl ester in 400 ml of benzene at room temperature and then, using a water separator, heated under reflux for 41/2 hours. After cooling to room temperature, the benzenic reaction solution is diluted with 500 ml of ethyl acetate, washed twice using 80 ml of 10% sodium carbonate solution each time and twice using 50 ml of water each time, dried over sodium sulfate and filtered. The solvent mixture is evaporated off. The yellow oil that remains is crystallised by trituration with diisopropyl ether. The beige-coloured crystals melt at 36°-37° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 41/2 hours
  3. washwashed twice
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customThe solvent mixture is evaporated off
  7. customThe yellow oil that remains is crystallised by trituration with diisopropyl ether
  8. custommelt at 36°-37° C.

Sources & evidence

ORD record
ord-03d4a26335444a6fb325f1faa8fd048a
Source dataset
uspto-grants-1995_02
Patent number
US05393766

Reaction notes

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