Ammonia → Thionyl Chloride

HRID 2220110Notes

Reaction equation

HRID 2220110 reaction equation
[Cl:1][C:2]1[C:3]([Cl:11])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7](O)=O.[O:12]=[S:13]([Cl:15])[Cl:14].[NH3:16]>>[Cl:11][C:3]1[C:2]([Cl:1])=[CH:10][C:6]([C:7]#[N:16])=[CH:5][N:4]=1.[O:12]=[S:13]([Cl:15])[Cl:14]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24386Thionyl ChlorideHCID 2479875,6-Dichloronicotinic acid

Product 2

HCID 24386Thionyl ChlorideHCID 128784645,6-Dichloropyridine-3-carbonitrile

Procedure

2,3-Dichloro 5-cyano pyridine 4 was prepared from 5,6-Dichloronicotinic acid (ALDRICH). The acid was converted to the acid chloride by treatment with excess SOCl2 and refluxed for 1.5 hours. The intermediate acid chloride was reacted with ammonia (aqueous) to get the primary amide which on dehydration with excess SOCl2 at reflux condition afforded 2, 3-Dichloro 5-cyano pyridine 4. [Ref. George et al J. Org. Chem, 1979, 44, 2697.]

Workup

  1. temperaturerefluxed for 1.5 hours

Sources & evidence

ORD record
ord-65feb5be5904477f952ae700c52e2641
Source dataset
uspto-grants-2008_08
Patent number
US07417045B2

Reaction notes

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