2,6-Difluorobenzoyl isocyanate → Diphenyl Ether

HRID 1415575Notes

Reaction equation

HRID 1415575 reaction equation
FC1C=CC=C(F)C=1C(N=C=O)=O.Cl[C:15]1[CH:29]=[C:28]([N+]([O-])=O)[CH:27]=[CH:26][C:16]=1[O:17][C:18]1[CH:24]=[CH:23][C:21](N)=[C:20](C)[CH:19]=1>C1(C)C=CC=CC=1>[C:18]1([O:17][C:16]2[CH:15]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:19]=[CH:20][CH:21]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 27333692,6-Difluorobenzoyl isocyanateHCID 214832554-(2-Chloro-4-nitrophenoxy)-2-methylaniline

Product 1

HCID 7583Diphenyl Ether

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of 3.7 g (0.02 mole) of 2,6-difluorobenzoylisocyanate in 20 ml of toluene was added dropwise at 50° C to a solution of 5.6 g (0.02 mole) of 4-(2'-chloro-4'-nitrophenoxy)-2-methylaniline in 100 ml of toluene. The batch was stirred for 1 hour at 60° C. The substance which separated out was filtered off after cooling the reaction mixture to 20° C and was washed with toluene and petroleum ether. After drying, 7 g (75% of theory) of 2-chloro-4-nitro-3'-methyl-4'-[N-(N'-2,6-difluorobenzoyl))-ureido]-diphenyl ether of melting point 190° C were obtained.

Workup

  1. customThe substance which separated out
  2. filtrationwas filtered off
  3. temperatureafter cooling the reaction mixture to 20° C
  4. washwas washed with toluene and petroleum ether
  5. customAfter drying

Sources & evidence

ORD record
ord-3817a9187257478e835c1dcf1dd8fc52
Source dataset
uspto-grants-1977_01
Patent number
US04005223

Reaction notes

Loading…