Thionyl Chloride → HCID 68579065, compound

HRID 273077Notes

Reaction equation

HRID 273077 reaction equation
[ClH:1].[CH:2]([N:5]1[CH2:8][CH:7]([CH2:9]O)[CH2:6]1)([CH3:4])[CH3:3].S(Cl)([Cl:13])=O>ClCCl>[ClH:13].[Cl:1][CH2:9][CH:7]1[CH2:8][N:5]([CH:2]([CH3:4])[CH3:3])[CH2:6]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 68575734(1-Isopropylazetidin-3-yl)methanol hydrochloride

Product 1

HCID 68579065HCID 68579065, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(1-isopropylazetidin-3-yl)methanol hydrochloride (2.6 g, 15.7 mmol) was dissolved in dichloromethane (50 ml) and cooled to 0° C. Thionyl chloride (1.4 ml, 19.2 mmol) was added dropwise over 5 min. The reaction mixture was then stirred whilst warming to ambient temperature. Stirred at ambient temperature for 48 hours. The reaction mixture was concentrated in vacuo and azeotroped with toluene (40 ml) to give the title compound as a beige hygroscopic powder (2.8 g, 99%). LRMS ESI+ m/z 148/150 [M+H]+ (CI isotopes).

Workup

  1. temperaturewhilst warming to ambient temperature
  2. stirringStirred at ambient temperature for 48 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customazeotroped with toluene (40 ml)

Sources & evidence

ORD record
ord-18d6e1fc4fb24465aa3f87e8ba92bbe4
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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