Thionyl Chloride → HCID 178499150, compound

HRID 2110186Notes

Reaction equation

HRID 2110186 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-f39a0795ab92424991064147fd759501
Source dataset
uspto-grants-2009_04
Patent number
US07517874B2

Reaction notes

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