Sodium hydride → 1-[2-Cyano-2-(2-methoxyphenyl)-3-(tetrahydrofuran-2-yl)propyl]-1,2,4-triazole

HRID 2255398Notes

Reaction equation

HRID 2255398 reaction equation
COC1C=CC=CC=1C(CC1CCCCO1)C#N.[H-].[Na+].ClCN1C=NC=N1.[C:28]([C:30]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=1[O:50][CH3:51])([CH2:37][CH:38]1[CH2:43][CH2:42]C[CH2:40][O:39]1)[CH2:31][N:32]1[CH:36]=[N:35][CH:34]=[N:33]1)#[N:29]>CCCCCC.CN(C=O)C.CS(C)=O>[C:28]([C:30]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=1[O:50][CH3:51])([CH2:37][CH:38]1[CH2:43][CH2:42][CH2:40][O:39]1)[CH2:31][N:32]1[CH:36]=[N:35][CH:34]=[N:33]1)#[N:29]

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 37438821-Chloromethyl-1H-1,2,4-triazoleHCID 197380281-[2-Cyano-2-(2-methoxyphenyl)-3-(tetrahydropyran-2-yl)propyl]-1,2,4-triazoleHCID 19738046HCID 19738046, compound

Product 1

HCID 197380321-[2-Cyano-2-(2-methoxyphenyl)-3-(tetrahydrofuran-2-yl)propyl]-1,2,4-triazoleYield 56%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

This compound was prepared using the procedure described in Example 2b except using 27.0 g. (0.110 mole) of 2-(2-methoxyphenyl)-3-(tetrahydropyran-2-yl)propionitrile, 6.6 g. (0.165 mole) of 60% sodium hydride which had been washed with hexane to remove the mineral oil originally present, 19 g. (0.165 mole) of 1-(chloromethyl)-1,2,4-triazole, and 400 ml. of a 1 to 1 mixture of DMSO and DMF. The 1-[2-cyano-2-(2-methoxyphenyl)-3-(tetrahydropyran-2-yl)propyl]-1,2,4-triazole, 20.0 g. (56% yield), was obtained as a solid, melting point 120°-121° C.

Workup

  1. customThis compound was prepared
  2. customto remove the mineral oil originally present
  3. custom(56% yield), was obtained as a solid, melting point 120°-121° C.

Sources & evidence

ORD record
ord-3f32ed3656b444dab0da71597f7f6667
Source dataset
uspto-grants-1993_08
Patent number
US05240925

Reaction notes

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