Thionyl Chloride → HCID 20368183, compound

HRID 1414245Notes

Reaction equation

HRID 1414245 reaction equation
P(Cl)(Cl)Cl.P(Br)(Br)Br.P(F)(F)F.S(Cl)([Cl:15])=O.[NH2:17][C:18]1[N:22]([CH2:23][CH2:24]O)[N:21]=[C:20]([C:26]2[N:27]([CH3:34])[C:28]([N+:31]([O-:33])=[O:32])=[CH:29][N:30]=2)[C:19]=1[C:35]#[N:36]>CN(C)C=O.C1C=CC=CC=1>[NH2:17][C:18]1[N:22]([CH2:23][CH2:24][Cl:15])[N:21]=[C:20]([C:26]2[N:27]([CH3:34])[C:28]([N+:31]([O-:33])=[O:32])=[CH:29][N:30]=2)[C:19]=1[C:35]#[N:36]

Participants

8

Reactant 5

HCID 24386Thionyl Chloride2×HCID 24387Phosphorus trichlorideHCID 24614Phosphorus tribromideHCID 62665Phosphorus trifluorideHCID 20368169HCID 20368169, compound

Product 1

HCID 20368183HCID 20368183, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6228DimethylformamideSolvent

Procedure

The haloalkyl imidazolyl pyrazoles, such as 5-amino-1-(haloalkyl)-3-(1-methyl-5-nitro-2-imidazolyl)pyrazole-4-carbonitrile, are prepared by reacting the corresponding hydroxyalkyl compound with a halogenating agent such as phosphorus trichloride, phosphorus tribromide, phosphorus trifluoride, thionyl chloride and the like. Thus, 5-amino-1-(β-hydroxyethyl)-3-(1-methyl-5-nitro-2-imidazolyl)pyrazole-4-carbonitrile, is allowed to react with thionyl chloride in an inert solvent such as benzene, in the presence of a small amount of dimethylformamide to yield 5-amino-1-(β-chloroethyl)-3-(1-methyl-5-nitro-2-imidazolyl)pyrazole-4-carbonitrile.

Sources & evidence

ORD record
ord-dcddf8eb31f74723896f4d58d4b1f3a0
Source dataset
uspto-grants-1977_01
Patent number
US04001230

Reaction notes

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