Phosgene → HCID 20383505, compound

HRID 26017Notes

Reaction equation

HRID 26017 reaction equation
Cl.[CH3:2][NH:3][C:4]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:5]=1[CH3:11].[C:12]([Cl:15])(Cl)=[O:13]>C1C=CC=CC=1>[CH3:11][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]([CH3:10])[C:4]=1[N:3]([CH3:2])[C:12]([Cl:15])=[O:13]

Participants

4

Reactant 2

HCID 6371Phosgene2×HCID 17352627N,2,6-Trimethylaniline hydrochloride

Product 1

HCID 20383505HCID 20383505, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Into a suspension of 121.1 g. (0.71 moles) of N,2,6-trimethylaniline hydrochloride in 1 l. of benzene at reflux is bubbled an excess of phosgene (0.175 ml. of liquid or 1.6 moles). After introduction of the phosgene, the mixture is refluxed for 1 hour and then 700 ml. of benzene removed by distillation at slightly reduced pressure. After the phosgene is gone the residue is triturated with hexane (300 ml.), filtered and dried to give 2,6-dimethylphenyl-N-methylcarbamoyl chloride (m.p. 79°-80° C.).

Workup

  1. additionInto a suspension of 121.1 g
  2. customof benzene removed by distillation at slightly reduced pressure
  3. customis triturated with hexane (300 ml.)
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-e305e17adb2d4e95821908e4fd7d3c41
Source dataset
uspto-grants-1979_04
Patent number
US04147804

Reaction notes

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