Chloroform → HCID 23316382, compound

HRID 1982379Notes

Reaction equation

HRID 1982379 reaction equation
C(Cl)(Cl)Cl.[Cl:5][C:6]1([CH:20]=[CH:19]N=[C:17]([CH:21]([OH:29])[C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[CH2:16]1)C(NC1C=CC=CC=1)=O.C([N:32]([CH2:35][CH3:36])[CH2:33][CH3:34])C.P(Br)(Br)Br>O>[Cl:5][C:6]1[CH:20]=[CH:19][C:35]2[N:32]=[C:33]([C:34]3[CH:34]=[CH:33][N:32]=[CH:35][CH:36]=3)[O:29][CH:21]([C:22]3[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=3)[C:17]=2[CH:16]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 24614Phosphorus tribromideHCID 86740862HCID 86740862, compound

Product 1

HCID 23316382HCID 23316382, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To chloroform (300 ml), 4-chloro-2-(4-chloro-α-hydroxybenzyl)-isonicotinanilide (12.4 g) and triethylamine (5.0 ml) were added. With stirring and under cooling with ice, phosphorus tribromide (9.1 g) was added slowly, and the stirring was continued for 1 hour. Following another 3-hour stirring at room temperature, the reaction mixture was poured into water. The chloroform layer was thoroughly washed with water and subsequently dried. The chloroform was completely distilled off under vacuum. Upon recrystallization from a mixed solvent of ethyl acetate and n-hexane, the titled compound was obtained in an amount of 10.1 g (yield: 85%). m.p. 140°-141° C.

Workup

  1. additionwas added slowly
  2. waitFollowing another 3-hour
  3. stirringstirring at room temperature
  4. washThe chloroform layer was thoroughly washed with water
  5. customsubsequently dried
  6. distillationThe chloroform was completely distilled off under vacuum
  7. customUpon recrystallization from a mixed solvent of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-75301921d7ab4bba90cab30a240f9bb4
Source dataset
uspto-grants-1986_06
Patent number
US04596801

Reaction notes

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