Ethyl (chloroformyl)acetate → HCID 178469834, compound

HRID 1980715Notes

Reaction equation

HRID 1980715 reaction equation
[C:1]([NH:4][C:5]([NH2:7])=[S:6])(=[NH:3])[NH2:2].[Cl:8][CH:9]([CH:15]=O)[C:10]([O:12][CH2:13][CH3:14])=[O:11]>C(O)C>[ClH:8].[NH:4]([C:5]1[S:6][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:15][N:7]=1)[C:1]([NH2:2])=[NH:3]

Participants

4

Reactant 2

HCID 118030Ethyl (chloroformyl)acetate3×HCID 178513045HCID 178513045, compound

Product 1

HCID 178469834HCID 178469834, compoundYield 41.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of amidinothiourea (117 g; 0.99 mole) and ethyl chloro-α-formylacetate (150 g; 1.0 mole) in 3.5 liters of absolute ethanol was stirred at ambient temperature for 18 hours and then heated at reflux temperature for 1 hour. At this time additional ethyl chloro-α-formylacetate (20.0 g; 0.13 mole) was added and 1 hour later another 20.0 g of ethyl chloro-α-formylacetate was added. After 2 hours of additional heating at reflux temperature, the reaction mixture was evaporated under reduced pressure and the residue triturated with 1.5 liters of acetone and filtered to give 103 g of product. Recrystallization from 2-propanol yielded the title compound, mp 204°-206°.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 1 hour
  3. additionwas added
  4. temperatureAfter 2 hours of additional heating
  5. temperatureat reflux temperature
  6. customthe reaction mixture was evaporated under reduced pressure
  7. customthe residue triturated with 1.5 liters of acetone
  8. filtrationfiltered

Sources & evidence

ORD record
ord-2cc0ab57356c4493b411b97db4a1438f
Source dataset
uspto-grants-1985_04
Patent number
US04510309

Reaction notes

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