Hydrochloric Acid → HCID 54504810, compound

HRID 614520Notes

Reaction equation

HRID 614520 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)N)([O-:3])=[O:2].[ClH:11].[Cl-].[N+](C1C=C([N+]#N)C=CC=1)([O-])=O.[Cl:24][C:25](=[CH2:28])[C:26]#[N:27]>O.CC(C)=O.C(O)(=O)C>[Cl:24][C:25]([Cl:11])([CH2:28][C:6]1[CH:8]=[CH:9][CH:10]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[C:26]#[N:27]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 74233-NitroanilineHCID 701982-ChloroacrylonitrileHCID 117886903-nitrobenzenediazonium Chloride

Product 1

HCID 54504810HCID 54504810, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 180AcetoneSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

138 g (1 mole) of m-nitro-aniline are slowly added in a 2-liter reactor to a mixture of 300 ml of concentrated HCl, 150 ml of water and 150 ml of acetic acid. The mixture is heated until the amine hydrochloride dissolves, whereafter the mixture is cooled to 0° C. with vigorous agitation. With the temperature remaining between 0° and 3° C., 70 g of NaHO2 dissolved in 150 ml of H2O are added.. The m-nitro-benzene-diazonium chloride solution is added simultaneously with an aqueous solution of 25 g of CuCl2.2H2O to a solution of 87 g of α-chloro-acrylonitrile in 150 ml of acetone. The temperature is kept at 30° C. Evolution of nitrogen ceases after about 6 hours. The α,α-dichloro-β-(3-nitrophenyl)propionitrile is extracted with benzene, washed in sodium hydroxide, then washed with water. After drying and removal of the solvent the product is distilled at low pressure. 215 g of α,α-dichloro-β-(3-nitrophenyl)propionitrile, corresponding to an 88% yield, are obtained, in the form of a slightly pinkish oil distilling at 140° C. at a pressure of 0.1 mm.

Workup

  1. dissolutiondissolves, whereafter the mixture
  2. customremaining between 0° and 3° C.
  3. additionare added
  4. customis kept at 30° C
  5. extractionThe α,α-dichloro-β-(3-nitrophenyl)propionitrile is extracted with benzene
  6. washwashed in sodium hydroxide
  7. washwashed with water
  8. customAfter drying
  9. customremoval of the solvent the product
  10. distillationis distilled at low pressure

Sources & evidence

ORD record
ord-e2ee8034627f42b286a24988fb41c6a4
Source dataset
uspto-grants-1979_03
Patent number
US04145362

Reaction notes

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