Water → 1-Cyano-2-(2,4-Dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl)-2-propanol

HRID 1979919Notes

Reaction equation

HRID 1979919 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([CH2:12][N:13]2[CH:17]=[N:16][CH:15]=[N:14]2)[CH2:11][O:10]1.[C-:18]#[N:19].[Na+].O>CN(C)C=O>[C:18]([CH2:11][C:9]([C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1])([OH:10])[CH2:12][N:13]1[CH:17]=[N:16][CH:15]=[N:14]1)#[N:19]

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 104232291H-1,2,4-Triazole, 1-[[2-(2,4-dichlorophenyl)oxiranyl]methyl]-

Product 1

HCID 133903931-Cyano-2-(2,4-Dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl)-2-propanolYield 63.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)oxirane (1.09 g) and sodium cyanide (0.6 g) in dimethylformamide (30 ml) were heated at 65°-70° C. for 1 hour. The reaction mixture was then cooled, poured into water (150 ml), and extracted with ethyl acetate (3×25 ml). The combined organic extracts were washed with saturated aqueous brine, dried (Na2SO4) and evaporated to dryness to give a pale yellow solid (0.76 g) which was triturated with ether. The residual solid was recrystallised from ether/methanol to give the title compound 285 mg (24%), m.p. 217°-219° C. Found: C,48.3; H,3.4; N,18.4. Calculated for C12H10Cl2N4O: C,48.5; H,3.4; N,18.8%.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. extractionextracted with ethyl acetate (3×25 ml)
  3. washThe combined organic extracts were washed with saturated aqueous brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-b05572d668654bccac1b498313d69d10
Source dataset
uspto-grants-1984_11
Patent number
US04483863

Reaction notes

Loading…