Dimethylformamide → HCID 17393332, compound

HRID 911633Notes

Reaction equation

HRID 911633 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][N:10]([CH:12]=O)C>O>[CH2:1]([NH:8][C:9]1[CH:4]=[CH:3][C:2]([C:1]#[N:8])=[CH:12][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 7504Benzylamine

Product 1

HCID 17393332HCID 17393332, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Heat 6-chloroniconitrile (0.58 g, 4.2 mmol) and benzylamine (4.6 mL, 42 mmol) in anhydrous DMF (3 mL) at 120° C. for 4.5 h. Cool at room temperature. Dilute with water and extract with EtOAc. Wash the organic phase with brine, dry over MgSO4, filter, and concentrate in vacuo. Purify by chromatography on silica gel eluting sequentially with hexane/EtOAc (4:1, 2:1, 1:2) to give the desired intermediate as a white solid (840 mg, 96%). MS (ES+) m/z: 210 (4+H)+.

Workup

  1. extractionextract with EtOAc
  2. washWash the organic phase with brine
  3. dry with materialdry over MgSO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customPurify by chromatography on silica gel eluting sequentially with hexane/EtOAc (4:1, 2:1, 1:2)

Sources & evidence

ORD record
ord-627c7e05e9e74c178797e52b92185240
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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