3-Aminopropionitrile → 3-[N-{2-nitro-5-(2-chloro-4-isopropylsulphonylphenoxy)phenyl}amino]propionitrile

HRID 64760

Reaction equation

HRID 64760 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([S:8]([CH:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[C:17]([N+:24]([O-])=O)[CH:16]=1.[NH2:27][CH2:28][CH2:29][C:30]#N.C([O-])(=O)/C=C/C([O-])=O.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N+:21]([C:18]1[CH:19]=[CH:20][C:15]([O:14][C:3]2[CH:4]=[CH:5][C:6]([S:8]([CH:11]([CH3:12])[CH3:13])(=[O:10])=[O:9])=[CH:7][C:2]=2[Cl:1])=[CH:16][C:17]=1[NH:24][CH2:30][CH2:29][C:28]#[N:27])([O-:23])=[O:22]

Participants

6

Reactant 4

HCID 16473-AminopropionitrileHCID 11430Potassium CarbonateHCID 5460307FumarateHCID 202373452-Chloro-4-isopropylsulphonyl-(3,4-dinitrophenoxy)benzene

Product 1

HCID 202373333-[N-{2-nitro-5-(2-chloro-4-isopropylsulphonylphenoxy)phenyl}amino]propionitrileYield 70.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4.0 g of 2-chloro-4-isopropylsulphonyl-(3,4-dinitrophenoxy)benzene and 3.85 g of 3-aminopropionitrile. 0.5 fumarate in 100 ml of acetonitrile, to which 4.1 g of potassium carbonate was added, was refluxed for 6 hours. After evaporation the residue was dissolved in methylenechloride an extracted with water. After washing with water the organic layer was filtered and reduced. Recrystallisation from methanol yielded 3.0 g of the desired product; m.p. 140° C.

Workup

  1. temperaturewas refluxed for 6 hours
  2. customAfter evaporation the residue
  3. dissolutionwas dissolved in methylenechloride
  4. extractionan extracted with water
  5. washAfter washing with water the organic layer
  6. filtrationwas filtered
  7. customRecrystallisation from methanol

Sources & evidence

ORD record
ord-59d1622462e9450283df71a7ce662383
Source dataset
uspto-grants-1986_09
Patent number
US04609753

Linked notes

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