Sulfuric Acid → HCID 53914136, compound

HRID 1074624Notes

Reaction equation

HRID 1074624 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:14]=O)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[NH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[CH:14][NH:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 5641Carbamic acid, ethyl esterHCID 13174739HCID 13174739, compound

Product 1

HCID 53914136HCID 53914136, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Then, 14.2 g of ethyl p-chlorophenyl-(α-formyl)acetate and 6.5 g of urethane were added to 50 ml of toluene containing 0.3 ml of concentrated sulfuric acid, and the mixture was heated at reflux while distilling out water which was formed during the reaction until no further water was distilled out. Thereafter, the solvent was distilled off, and the residue was extracted with diethyl ether while hot. The solvent was distilled off from the extract to obtain 13.7 g of ethyl p-chlorophenyl-(α-ethoxycarbonylaminomethylene)acetate having a melting point of 72° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux
  3. distillationwhile distilling out water which
  4. customwas formed during the reaction until no further water
  5. distillationwas distilled out
  6. distillationThereafter, the solvent was distilled off
  7. extractionthe residue was extracted with diethyl ether while hot
  8. distillationThe solvent was distilled off from the
  9. extractionextract

Sources & evidence

ORD record
ord-1b06b362c59742b99a3aae5ae1cefc92
Source dataset
uspto-grants-1983_07
Patent number
US04393210

Reaction notes

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