Phosgene → HCID 23461740, compound

HRID 1733165Notes

Reaction equation

HRID 1733165 reaction equation
[CH2:1]([NH:4][C:5](=O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:2]=[CH2:3].C(Cl)(Cl)=O>CN(C)C=O.O1CCCC1.C1C=CC=CC=1>[CH2:13]([O:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[C:5]1[NH:4][CH:1]=[CH:2][CH:3]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 6371PhosgeneHCID 4946393HCID 4946393, compound

Product 1

HCID 23461740HCID 23461740, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 22633675Benzene tetrahydrofuranSolvent

Procedure

2.7 (10 millimoles) of o-benzyloxybenzoic acid allylamide in 20 ml of a 20 per cent strength by weight solution of phosgene in tuluene are stirred, in the presence of 2 drops of dimethylformamide, at room temperature overnight. The residue which remains after distilling off the toluene under reduced pressure at 40° C. bath temperature is taken up in 30 ml of tetrahydrofuran, and the solution is filtered through a pad of glass wool and introduced, in the course of 45 minutes, into an ice-cooled solution of 4.0 g (30 millimoles) of potassium tert.-butylate in 60 ml of a 1:1 (by volume) tetrahydrofuran/benzene mixture, under argon as protective gas. 10 minutes after completion of the addition, the solvent is distilled off under reduced pressure, the residue is partitioned between methylene chloride and water, and the water is extracted twice with methylene chloride.

Workup

  1. distillationafter distilling off the toluene under reduced pressure at 40° C. bath temperature
  2. filtrationthe solution is filtered through a pad of glass wool
  3. additionintroduced, in the course of 45 minutes, into an ice-
  4. addition10 minutes after completion of the addition
  5. distillationthe solvent is distilled off under reduced pressure
  6. customthe residue is partitioned between methylene chloride and water
  7. extractionthe water is extracted twice with methylene chloride

Sources & evidence

ORD record
ord-e3144ad2c4b74de7abf284f97c4a0b9c
Source dataset
uspto-grants-1980_12
Patent number
US04240964

Reaction notes

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