Phenyl chloroformate → Phenyl (2,3-dichlorophenoxy)carbamate

HRID 1195605Notes

Reaction equation

HRID 1195605 reaction equation
[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[O:4][NH2:5].Cl[C:12]([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:13]>N1C=CC=CC=1.ClCCl>[C:15]1([O:14][C:12](=[O:13])[NH:5][O:4][C:3]2[CH:6]=[CH:7][CH:8]=[C:9]([Cl:10])[C:2]=2[Cl:1])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 15891Phenyl chloroformateHCID 13574896HCID 13574896, compound

Product 1

HCID 13746370Phenyl (2,3-dichlorophenoxy)carbamateYield 83%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

9.10 g (51.1 mmole) of 2,3-dichlorophenoxyamine was dissolved in 7.5 ml of pyridine and 70 ml of dichloromethane, and the solution was cooled to -10° C. Then, 30 ml of a dichloromethane solution containing 7.28 g (46.5 mmole) of phenyl chloroformate was dropwise added thereto over a period of 1 hour, and the mixture was stirred at a temperature of from -10° to 25° C. for 6 hours. The solvent was distilled off under reduced pressure, and 300 ml of ethyl acetate was added. The mixture was washed with water and a saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off under reduced pressure, and the residue thereby obtained was recrystallized from toluene/hexane, whereby 11.5 g of the desired product was obtained as light brown crystals (yield: 83%)

Workup

  1. additionwas dropwise added
  2. distillationThe solvent was distilled off under reduced pressure, and 300 ml of ethyl acetate
  3. additionwas added
  4. washThe mixture was washed with water
  5. dry with materiala saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate
  6. distillationEthyl acetate was distilled off under reduced pressure
  7. customthe residue thereby obtained
  8. customwas recrystallized from toluene/hexane

Sources & evidence

ORD record
ord-7ca736f8f02f4f73b996df1b18e822dd
Source dataset
uspto-grants-1992_05
Patent number
US05112385

Reaction notes

Loading…