Ethyl 2-chloroacetoacetate → HCID 12813041, compound

HRID 1902463Notes

Reaction equation

HRID 1902463 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:6]([NH2:8])=O.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:17].[CH2:30]([O:32][C:33](=[O:39])[CH:34](Cl)[C:35]([CH3:37])=O)[CH3:31]>C(Cl)(Cl)Cl>[CH2:30]([O:32][C:33]([C:34]1[S:17][C:6]([C:5]2[CH:4]=[C:3]([O:2][CH3:1])[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[CH:9]=2)=[N:8][C:35]=1[CH3:37])=[O:39])[CH3:31]

Participants

5

Reactant 3

HCID 11858Ethyl 2-chloroacetoacetateHCID 14817Phosphorus sulfide (P2S5)HCID 18334Benzamide, 3,4,5-trimethoxy-

Product 1

HCID 12813041HCID 12813041, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In a round bottom flask, 21.1 g (0.1 mol) of 3,4,5-trimethoxybenzamide, 4.4 g (0.02 mol) of diphosphorus pentasulfide and 250 ml of chloroform were introduced and after attaching a reflux condenser to the flask, the content was heated for 2 hours while refluxing. Then, 19.8 g (0.12 mol) of alphachloroacetoacetic ethyl ester was added to the content of the flask, and the mixture was heated for 5 hours while refluxing. After filtering the reaction mixture while hot and condensing the filtrate to dryness, activated carbon was added to the residue and the mixture was recrystallized from ethanol. The product consisting of needle-like crystals light cream in colour amounting to 28.2 g was thus obtained at a yield of 84%. The crystals melted at 118° to 119° C.

Workup

  1. temperaturethe content was heated for 2 hours
  2. temperaturewhile refluxing
  3. temperaturethe mixture was heated for 5 hours
  4. temperaturewhile refluxing
  5. filtrationAfter filtering the reaction mixture while hot and
  6. customcondensing the filtrate to dryness, activated carbon
  7. additionwas added to the residue
  8. customthe mixture was recrystallized from ethanol
  9. customwas thus obtained at a yield of 84%

Sources & evidence

ORD record
ord-56b652e49b374a6ba95dcc21570e6050
Source dataset
uspto-grants-1982_12
Patent number
US04363813

Reaction notes

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