Chloroform → 4-(Chlorodiphenylmethyl)pyridine

HRID 1584027Notes

Reaction equation

HRID 1584027 reaction equation
[C:1]1([C:7](O)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(Cl)[Cl:22].S(Cl)(Cl)=O.C(N(CC)CC)C>C1C=CC=CC=1>[C:1]1([C:7]([Cl:22])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 74177alpha,alpha-Diphenyl-4-pyridinemethanol

Product 1

HCID 132158954-(Chlorodiphenylmethyl)pyridine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

92.1 g (0.353 mol) of diphenyl(4-pyridyl)methyl alcohol recrystallized from chloroform and 800 ml of simple-distillation benzene were charged in a 2-l three-necked flask provided with a stirrer and reflux condenser. The mixture was treated at 50° C. to form a suspension. 29.6 ml (0.407 mol) of thionyl chloride was poured in the suspension and the mixture was stirred under reflux for 1 h. The resulting solution was cooled to room temperature. 72.5 ml (0.522 mol) of triethylamine was added thereto and the mixture was stirred for 7 h. The reaction solution was filtered and the filtrate was concentrated to obtain crude diphenyl(4-pyridyl)methyl chloride.

Workup

  1. additionwere charged in a 2-l three-necked flask
  2. customprovided with a stirrer
  3. temperaturereflux condenser
  4. additionThe mixture was treated at 50° C.
  5. customto form a suspension
  6. temperatureunder reflux for 1 h
  7. stirringthe mixture was stirred for 7 h
  8. filtrationThe reaction solution was filtered
  9. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-d74a9b0b6cc54d989edb23870de457bc
Source dataset
uspto-grants-1985_11
Patent number
US04555574

Reaction notes

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