Water → HCID 54481946, compound

HRID 1733005Notes

Reaction equation

HRID 1733005 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][N:5]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13]Br)=[C:9]([Cl:15])[CH:8]=2)[CH:6]=1.[C-:16]#[N:17].[Na+].O>CS(C)=O>[Cl:15][C:9]1[CH:8]=[C:7]([N:5]2[CH:6]=[C:2]([Cl:1])[CH:3]=[N:4]2)[CH:12]=[CH:11][C:10]=1[CH2:13][C:16]#[N:17]

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 20303444HCID 20303444, compound

Product 1

HCID 54481946HCID 54481946, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

15 g of 4-chloro-1-(4-bromomethyl-3-chlorophenyl)pyrazole are added to 2.8 g of sodium cyanide in 67 ml of dimethylsulfoxide and stirred for 6.5 hours at room temperature. 300 ml of water are added dropwise and 12.3 g of 2-chloro-4-(4-chloropyrazol-1-yl)phenylacetonitrile are thus obtained. Chromatographing the latter with a mixture of cyclohexane/ethanol/ethyl acetate on silica gel, yields a product with a m.p. 139.5° to 140° C. (As by-product, 1,2-bis-[2-chloro-4-(4-chloropyrazol-1-yl)phenyl]propionic acid nitrile has formed; from this by-product the appropriate amide with m.p. 248° to 249.5° C. is obtained by saponification with concentrated sulfuric acid.)

Sources & evidence

ORD record
ord-aeee382bbe0f41ed821d6dcc31672287
Source dataset
uspto-grants-1980_12
Patent number
US04239901

Reaction notes

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