Thionyl Chloride → HCID 178499150, compound

HRID 535914Notes

Reaction equation

HRID 535914 reaction equation
[CH2:1]([N:8]([CH2:12][C:13]1[N:14]=[CH:15][NH:16][C:17]=1[C:18]([O:20][CH3:21])=[O:19])[CH2:9][CH2:10]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:24])=O>C(Cl)Cl>[ClH:24].[CH2:1]([N:8]([CH2:12][C:13]1[N:14]=[CH:15][NH:16][C:17]=1[C:18]([O:20][CH3:21])=[O:19])[CH2:9][CH2:10][Cl:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 178499151HCID 178499151, compound

Product 1

HCID 178499150HCID 178499150, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
44 °C

Procedure

To a solution of Intermediate 1D (0.94 g, 3.24 mmol) in DCM (30 mL) was added thionyl chloride (0.95 mL, 12.96 mmol). The resulting mixture was stirred at 44° C. overnight and allowed to cool to ambient temperature. The mixture was concentrated under reduced pressure, azeotroped with acetonitrile and dried under vacuum overnight to give Intermediate 1E in quantitative yield as a white solid which was used in the next step without further purification.

Workup

  1. temperatureto cool to ambient temperature
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customazeotroped with acetonitrile
  4. customdried under vacuum overnight

Sources & evidence

ORD record
ord-c8d5b72adee54506b4b87124fbffdcb6
Source dataset
uspto-grants-2014_10
Patent number
US08859538B2

Reaction notes

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