Ammonia → HCID 21704275, compound

HRID 1595181Notes

Reaction equation

HRID 1595181 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[NH:13][C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16]([OH:18])=[O:17])([O-])=O.[Cl-].[NH4+].N.[S-2].[Na+].[Na+]>O.C(O)C>[NH2:1][C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[NH:13][C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16]([OH:18])=[O:17]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 14804Sodium SulfideHCID 25517Ammonium ChlorideHCID 6275142-(2,4-Dinitroanilino)benzoic acid

Product 1

HCID 21704275HCID 21704275, compoundYield 67.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1.80 g (6 mmol) of 2-(2,4-dinitrophenylamino)benzoic acid, 2.66 g (42.6 mmol) of ammonium chloride, 2.4 ml of ammonia, concentrated, 52 ml of ethanol, and 21 ml of distilled water are combined at an internal temperature of 78° C. (bath temperature 90° C.). To this batch is added, in 3 portions, 4.44 g (20 mmol) of sodium sulfide (35% strength) and the mixture is stirred for one hour. The batch is suctioned off at room temperature and washed in succession with water and ether. The filtrate is concentrated to the aqueous phase and extracted by shaking with ethyl acetate. The organic phase is dried, filtered, and concentrated. The aqueous phase is acidified with 1N hydrochloric acid and suctioned off, thus obtaining 1.1 g of 2-(2-amino-4-nitrophenylamino)benzoic acid (processed without purification).

Workup

  1. customare combined at an internal temperature of 78° C. (bath temperature 90° C.)
  2. customis suctioned off at room temperature
  3. washwashed in succession with water and ether
  4. concentrationThe filtrate is concentrated to the aqueous phase
  5. extractionextracted
  6. stirringby shaking with ethyl acetate
  7. customThe organic phase is dried
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-18638cf234b1427f8087cadeecb0efd1
Source dataset
uspto-grants-2001_09
Patent number
US06288065B1

Reaction notes

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