Thionyl Chloride → HCID 68576193, compound

HRID 272994Notes

Reaction equation

HRID 272994 reaction equation
[CH:1]([N:14]1[CH2:17][CH:16]([CH2:18]O)[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:22])=O>ClCCl>[ClH:22].[CH:1]([N:14]1[CH2:17][CH:16]([CH2:18][Cl:22])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 2758715(1-Benzhydrylazetidin-3-yl)methanol

Product 1

HCID 68576193HCID 68576193, compoundYield 168.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
2.5 °C

Procedure

(1-Benzhydryl-azetidin-3-yl)-methanol (3.07 g, 12.1 mmol) was dissolved in dichloromethane (60 ml). The reaction was cooled to 0-5° C. and thionyl chloride (1.07 ml, 14.6 mmol) was added slowly. The reaction was allowed to warm to room temperature and stirred for 18 hours. The reaction was concentrated in vacuo and azeotroped with toluene (3×20 ml) to give the title compound (3.8 g, 100%) as a pale brown solid.

Workup

  1. temperatureto warm to room temperature
  2. concentrationThe reaction was concentrated in vacuo
  3. customazeotroped with toluene (3×20 ml)

Sources & evidence

ORD record
ord-487dd085125e4edcbd1de025078c0b97
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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