Ammonia → HCID 178509708, compound

HRID 1953242Notes

Reaction equation

HRID 1953242 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([NH2:11])[CH:5]=1)([O-:3])=[O:2].[C:12]([C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21](O)=O)=[CH:16][CH:15]=1)#[N:13].N>P(Cl)(Cl)(Cl)=O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]2[NH:10][C:21]([CH2:20][C:17]3[CH:18]=[CH:19][C:14]([C:12]#[N:13])=[CH:15][CH:16]=3)=[N:11][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 795874-Cyanophenylacetic acidHCID 51117914-Nitro-1,2-phenylenediamine

Product 1

HCID 178509708HCID 178509708, compound

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

3.1 g (0.02 mol) of 4-nitro-o-phenylenediamine and 3.7 g (0.023 mol) of 4-cyanophenylacetic acid are refluxed for 2 hours in 30 ml of phosphorus oxychloride. After cooling the mixture is neutralised with concentrated ammonia and extracted with ethyl acetate. The combined organic extracts are dried over sodium sulphate and concentrated by evaporation. The residue is chromatographed on silica gel, eluting with methylene chloride/methanol (50:1). The desired fractions are concentrated by evaporation, the residue is triturated with ethyl acetate/ether, suction filtered and dried.

Workup

  1. temperatureAfter cooling the mixture
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic extracts are dried over sodium sulphate
  4. concentrationconcentrated by evaporation
  5. customThe residue is chromatographed on silica gel
  6. washeluting with methylene chloride/methanol (50:1)
  7. concentrationThe desired fractions are concentrated by evaporation
  8. customthe residue is triturated with ethyl acetate/ether, suction
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-dcf9789921fe416c998967797e4fa51f
Source dataset
uspto-grants-2000_09
Patent number
US06114532

Reaction notes

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