Hydrochloric Acid → 2,6-Dichloro-N-(((4-(2,2-dichloro-1,1-difluoroethoxy)phenyl)amino)carbonyl)-benzamide

HRID 426632Notes

Reaction equation

HRID 426632 reaction equation
[Cl:1][CH:2]([Cl:14])[C:3]([F:13])([F:12])[O:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1.Cl.[Cl:16][C:17]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:18]=1[C:19]([N:21]=[C:22]=[O:23])=[O:20]>C1(C)C(C)=CC=CC=1>[Cl:16][C:17]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:18]=1[C:19]([NH:21][C:22]([NH:11][C:8]1[CH:7]=[CH:6][C:5]([O:4][C:3]([F:12])([F:13])[CH:2]([Cl:1])[Cl:14])=[CH:10][CH:9]=1)=[O:23])=[O:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 30172134-(2,2-Dichloro-1,1-difluoroethoxy)anilineHCID 129127392,6-Dichlorobenzoyl isocyanate

Product 1

HCID 202023562,6-Dichloro-N-(((4-(2,2-dichloro-1,1-difluoroethoxy)phenyl)amino)carbonyl)-benzamideYield 463.9%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

In 200 milliliters of xylene, 11.5 grams (0.04 mole) of β,β-dichloro-α,α-difluoro-p-phenetidine.HCl and 3.6 grams (0.04 mole) of 2,6-dichlorobenzoyl isocyanate were refluxed with stirring for two hours. The xylene was thereafter removed by vacuum distillation. The residue which remained was mixed with 200 milliliters of hexane and a crystalline solid precipitated. This precipitated material was collected by suction filtration, washed with hexane and dried. The dried crude product was a light tan gummy solid melting at 160°-185° C. This crude product was purified by recrystallization from 60 milliliters of 83 percent aqueous acetic acid, leaving 85 grams of a white solid melting at 211°-213° C. (56 percent of theoretical). Nuclear magnetic resonance spectroscopy confirmed the structure as being ##STR13##

Workup

  1. customThe xylene was thereafter removed by vacuum distillation
  2. additionThe residue which remained was mixed with 200 milliliters of hexane
  3. customa crystalline solid precipitated
  4. filtrationThis precipitated material was collected by suction filtration
  5. washwashed with hexane
  6. customdried
  7. customThe dried crude product
  8. customThis crude product was purified by recrystallization from 60 milliliters of 83 percent aqueous acetic acid

Sources & evidence

ORD record
ord-7e0ba85edc174a53a9812a02292a176c
Source dataset
uspto-grants-1979_10
Patent number
US04170657

Reaction notes

Loading…