Dimethylformamide → HCID 17393332, compound

HRID 2041497Notes

Reaction equation

HRID 2041497 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 (M+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-0d5d2a4dced64502b51d3fee1ca6139c
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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