Sulfuric Acid → 2,2,3-Trichloropropiononitrile

HRID 1086416Notes

Reaction equation

HRID 1086416 reaction equation
ClCl.[Cl:3]C(=C)C#N.[Cl:8][C:9]([Cl:14])([CH2:12][Cl:13])[C:10]#[N:11].OS(O)(=O)=O.O=S(Cl)Cl.CN([CH:27]=[O:28])C>>[Cl:8][C:9]([Cl:14])([CH2:12][Cl:13])[C:10]#[N:11].[Cl:8][C:9]([Cl:14])([CH2:12][Cl:13])[C:27]([Cl:3])=[O:28]

Participants

8

Reactant 6

HCID 1118Sulfuric AcidHCID 6228DimethylformamideHCID 131332,2,3-TrichloropropiononitrileHCID 24386Thionyl ChlorideHCID 24526ChlorineHCID 701982-Chloroacrylonitrile

Product 2

HCID 131332,2,3-TrichloropropiononitrileHCID 19825918HCID 19825918, compound

Procedure

Firstly 2,2,3-trichloropropionitrile is prepared by adding chlorine to α-chloroacrylonitrile, as descibed by H. Brintzinger et al in Angew. Chemie, 1948, 60,p.311 and then the 2,2,3-trichloropropionitrile undergoes acid hydrolysis with 60% H2SO4 at 125° C. and for 5 hours in order to obtain the corresponding acid, as described by H. Laato in Suomen Kemistilehti, 1968, 41B, p.266. The acid is then treated by SOCl2 in the presence of a catalytic quantity of DMF at 40° to 50° C.and for 1 hour, which gives 2,2,3-trichloropropanoyl chloride, which is distilled at 50° C. under 2700 Pa (20 mm of Hg),the yield being 66%.

Workup

  1. customfor 5 hours in order to obtain the corresponding acid

Sources & evidence

ORD record
ord-e8550155bc914c07a6337288a079c78e
Source dataset
uspto-grants-1991_07
Patent number
US05030628

Reaction notes

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