Phosgene → HCID 54199066, compound

HRID 848056Notes

Reaction equation

HRID 848056 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].[CH:5](=[C:12]1[CH2:16][CH2:15][NH:14][C:13]1=[O:17])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(CCCC)CCCC)CCC>C(OCC)(=O)C>[CH:5](=[C:12]1[CH2:16][CH2:15][N:14]([C:1]([Cl:4])=[O:2])[C:13]1=[O:17])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 7622TributylamineHCID 264155HCID 264155, compound

Product 1

HCID 54199066HCID 54199066, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

2.0 g (20.5 mmols) of phosgene are added to a suspension of 3.0 g (18.6 mmols) of 3-benzylidene-2-pyrrolidinone 50 ml in abs. ethyl acetate at -20°. A solution of 3.8 g (20.5 mmols) of tri-n-butylamine in 20 ml of abs. ethyl acetate is added dropwise to this mixture at 0° to 5°. After stirring for 4 hours at room temperature, dry nitrogen is passed through the mixture for 30 minutes and the mixture is then concentrated. Water is added to the oily residue, whereupon the acid chloride precipitates in the solid form. It is filtered off and dried over P2O5 and KOH is a desiccator. 3.5 g (84.5%).

Workup

  1. customat -20°
  2. waitdry nitrogen is passed through the mixture for 30 minutes
  3. concentrationthe mixture is then concentrated
  4. additionWater is added to the oily residue, whereupon the acid chloride
  5. customprecipitates in the solid form
  6. filtrationIt is filtered off
  7. dry with materialdried over P2O5 and KOH

Sources & evidence

ORD record
ord-01ceb94cbe804dba814f90c399d457c0
Source dataset
uspto-grants-1981_10
Patent number
US04294827

Reaction notes

Loading…