Thionyl Chloride → 5-(6-Chlorohexyl)pyrimidine

HRID 1583413Notes

Reaction equation

HRID 1583413 reaction equation
[N:1]1[CH:6]=[C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]O)[CH:4]=[N:3][CH:2]=1.S(Cl)([Cl:16])=O>ClCCl>[N:1]1[CH:6]=[C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][Cl:16])[CH:4]=[N:3][CH:2]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 135575446-(Pyrimidin-5-yl)hexan-1-ol

Product 1

HCID 139997535-(6-Chlorohexyl)pyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 20.6 g of 5-pyrimidinehexanol in 80 ml of dichloromethane was cooled in an ice bath as a solution of 12.3 ml of thionyl chloride in 40 ml of dichloromethane was added dropwise. The mixture was stirred at room temperature for 1 hour and at reflux temperature for 1 hour, was concentrated, azeotroped with toluene, diluted with dichloromethane and washed with water, saturated sodium bicarbonate, and brine. Evaporation gave 22.3 g of 6-(5-pyrimidinyl)hexylchloride.

Workup

  1. additionwas added dropwise
  2. temperatureat reflux temperature for 1 hour
  3. concentrationwas concentrated
  4. customazeotroped with toluene
  5. additiondiluted with dichloromethane
  6. washwashed with water, saturated sodium bicarbonate, and brine
  7. customEvaporation

Sources & evidence

ORD record
ord-b418343612a74580886775645b219622
Source dataset
uspto-grants-1985_11
Patent number
US04551460

Reaction notes

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