Ethyl chloroformate → Ethyl [3,5-dichloro-4-(3,5-dichlorophenoxy)phenyl]carbamate

HRID 1277825Notes

Reaction equation

HRID 1277825 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:18])[CH:5]=[C:6]([Cl:17])[C:7]=1[O:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11]([Cl:16])[CH:10]=1.Cl[C:20]([O:22][CH2:23][CH3:24])=[O:21]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:18][C:20](=[O:21])[O:22][CH2:23][CH3:24])[CH:5]=[C:6]([Cl:17])[C:7]=1[O:8][C:9]1[CH:10]=[C:11]([Cl:16])[CH:12]=[C:13]([Cl:15])[CH:14]=1

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 23451841HCID 23451841, compound

Product 1

HCID 54304496Ethyl [3,5-dichloro-4-(3,5-dichlorophenoxy)phenyl]carbamate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
5 °C

Procedure

3,5-Dichloro-4-(3,5-dichlorophenoxy)benzenamine (0.1 mole) and pyridine (50 ml) are charged into a glass reaction vessel fitted with a mechanical stirrer and thermometer and are cooled to about 5° C. Ethyl chloroformate (0.125 mole) is added, with stirring, at about 5° C. Stirring is continued for a period of about 30 minutes at about 5° C., then for an additional 16 hours at room temperature. The mixture is then washed with 2 portions of water (50 ml), dried and the solventis then removed to yield the desired product ethyl [3,5-dichloro-4-(3,5-dichlorophenoxy)phenyl]carbamate.

Workup

  1. customfitted with a mechanical stirrer
  2. stirringStirring
  3. waitfor an additional 16 hours at room temperature
  4. washThe mixture is then washed with 2 portions of water (50 ml)
  5. customdried
  6. customthe solventis then removed

Sources & evidence

ORD record
ord-d0387e11e0a148d2931619ace8b2d3fa
Source dataset
uspto-grants-1981_07
Patent number
US04279637

Reaction notes

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