Dichloromethane → HCID 19349416, compound

HRID 2107769Notes

Reaction equation

HRID 2107769 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:5]=[C:6]([C:16]([CH3:20])([CH3:19])[C:17]#[N:18])[CH:7]=[C:8]([CH2:10][N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)[CH:9]=1.[C-:21]#[N:22].[K+].ClCCl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:17]([C:16]([C:6]1[CH:5]=[C:4]([CH2:3][C:21]#[N:22])[CH:9]=[C:8]([CH2:10][N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)[CH:7]=1)([CH3:20])[CH3:19])#[N:18]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 9032Potassium CyanideHCID 19349446HCID 19349446, compound

Product 1

HCID 19349416HCID 19349416, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent2×

Procedure

A mixture of the product from Example 28 (0.73 g), tetrabutylammonium bromide (0.01 g), potassium cyanide (0.52 g), dichloromethane (2 ml) and water (2 ml) was heated under reflux for 3 h. It was then cooled, water (20 ml) was added, and the mixture was extracted three times with ethyl acetate. The extracts were combined, dried and evaporated to dryness under reduced pressure, and the residue was purified by flash column chromatography, eluting with methanol:ethyl acetate (3:97 by volume), to give 3-(1-cyano-1-methylethyl)-5-(1H-1,2,4-triazol-1-ylmethyl)phenylacetonitrile. Nmr in deuteriochloroform: δ 8.18(1H,s), 8.0(1H,s), 7.42(1H,m), 7.38(1H,m), 7.18(1H,m), 5.4(2H,s), 3.78(2H,s), 1.72(6H,s).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 h
  3. temperatureIt was then cooled
  4. extractionthe mixture was extracted three times with ethyl acetate
  5. customdried
  6. customevaporated to dryness under reduced pressure
  7. customthe residue was purified by flash column chromatography
  8. washeluting with methanol:ethyl acetate (3:97 by volume)

Sources & evidence

ORD record
ord-7870961f494648eeb611e7c3f1646bfc
Source dataset
uspto-grants-1990_06
Patent number
US04935437

Reaction notes

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