Toluene → HCID 23461740, compound

HRID 2286517Notes

Reaction equation

HRID 2286517 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.C1(C)C=CC=CC=1.O1CCCC1>CN(C)C=O.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

7

Reactant 4

HCID 1140TolueneHCID 6371PhosgeneHCID 8028TetrahydrofuranHCID 4946393HCID 4946393, compound

Product 1

HCID 23461740HCID 23461740, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 241BenzeneSolvent

Procedure

2.7 g (10 millimoles) of o-benzyloxybenzoic acid allylamide in 20 ml of a 20% strength by weight solution of phosgene and toluene 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 glass wool and is 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) mixture of tetrahydrofuran and benzene, under argon as a 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 aqueous phase 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 glass wool
  3. additionis introduced, 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 aqueous phase is extracted twice with methylene chloride

Sources & evidence

ORD record
ord-de27e6ce962e406199c25926a939a59f
Source dataset
uspto-grants-1981_05
Patent number
US04267187

Reaction notes

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