Dimethylformamide → HCID 57635595, compound

HRID 535974Notes

Reaction equation

HRID 535974 reaction equation
[CH3:1][N:2]1[CH2:8][CH2:7][CH2:6][N:5]2[C:9]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:10][C:11]([C:12](O)=[O:13])=[C:4]2[CH2:3]1.S(Cl)([Cl:23])=O.CN(C=O)C>C(Cl)Cl>[CH3:1][N:2]1[CH2:8][CH2:7][CH2:6][N:5]2[C:9]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:10][C:11]([C:12]([Cl:23])=[O:13])=[C:4]2[CH2:3]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 57635120HCID 57635120, compound

Product 1

HCID 57635595HCID 57635595, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of intermediate 64C (0.12 g, 0.44 mmol) in 3 mL DCM was added thionyl chloride (0.16 mL, 2.21 mmol), followed by catalytic amount of DMF. The resulting mixture was stirred at 50° C. for 30 minutes, concentrated and the residual thionyl chloride was azeotroped with toluene. The resulting material 64D was dried under vacuum and used in the next step without purification.

Workup

  1. concentrationconcentrated
  2. customthe residual thionyl chloride was azeotroped with toluene
  3. dry with materialThe resulting material 64D was dried under vacuum
  4. customused in the next step without purification

Sources & evidence

ORD record
ord-e1a83089764d44019f17738f5e6d7c33
Source dataset
uspto-grants-2014_10
Patent number
US08859538B2

Reaction notes

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