Phosgene → 2,6-dimethyl-N-butylphenylcarbamoyl chloride

HRID 26020Notes

Reaction equation

HRID 26020 reaction equation
[CH2:1]([NH:5][C:6]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:13])[CH2:2][CH2:3][CH3:4].[C:14](Cl)([Cl:16])=[O:15]>C1(C)C=CC=CC=1>[CH3:13][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]([CH3:12])[C:6]=1[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:14]([Cl:16])=[O:15]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 5251001N-butyl-2,6-dimethylaniline

Product 1

HCID 544782032,6-dimethyl-N-butylphenylcarbamoyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 31.5 g. of N-butyl-2,6-dimethylaniline in 400 ml. of toluene is added 50 ml. of phosgene. The solution is heated to reflux and refluxed for 30 minutes. The solvent is then allowed to distill off (ca 350 ml.) and then cooled. The solution is evaporated in vacuo to a light oil which is then dissolved into hexane, filtered and the hexane evaporated off in vacuo to give a milky oil which is then distilled to give 2,6-dimethyl-N-butylphenylcarbamoyl chloride (b.p. 105° C./0.1 mm)

Workup

  1. additionTo a suspension of 31.5 g
  2. temperatureThe solution is heated
  3. temperatureto reflux
  4. temperaturerefluxed for 30 minutes
  5. distillationto distill off (ca 350 ml.)
  6. temperaturecooled
  7. customThe solution is evaporated in vacuo to a light oil which
  8. dissolutionis then dissolved into hexane
  9. filtrationfiltered
  10. customthe hexane evaporated off in vacuo
  11. customto give a milky oil which
  12. distillationis then distilled

Sources & evidence

ORD record
ord-8736cdf127324f3f856499f0788518fe
Source dataset
uspto-grants-1979_04
Patent number
US04147804

Reaction notes

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