Ammonia → Benzenesulfonamide, 3-nitro-4-(phenylamino)-

HRID 1576279Notes

Reaction equation

HRID 1576279 reaction equation
[NH3:1].[S:2](Cl)([OH:5])(=O)=[O:3].Cl[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15].[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)CCC>[C:18]1([NH:17][C:8]2[CH:13]=[CH:12][C:11]([S:2]([NH2:1])(=[O:5])=[O:3])=[CH:10][C:9]=2[N+:14]([O-:16])=[O:15])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 222Ammonia2×HCID 6115AnilineHCID 20028854HCID 20028854, compound

Product 1

HCID 82980Benzenesulfonamide, 3-nitro-4-(phenylamino)-

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

The dyestuff used in Example 204 had been prepared as follows: 900 parts of n-butanol saturated with ammonia are mixed with 550 parts of 79% 4-chloro-3-nitrobenzene sulphochloride and the mixture is stirred at 55° - 60°C for 1 hour. 200 Parts aniline were added and the mixture was heated to boiling temperature while slowly introducing ammonia, until the dyestuff formation was completed. After cooling, the crystallised product was filtered off with suction, washed with methanol and water and after drying there were obtained 460 parts 4-phenylamino-3-nitrobenzene-sulphonic acid amide = 92% of theory; m.p. 155°C.

Workup

  1. customhad been prepared
  2. temperaturethe mixture was heated
  3. temperatureAfter cooling
  4. filtrationthe crystallised product was filtered off with suction
  5. washwashed with methanol and water
  6. customafter drying there

Sources & evidence

ORD record
ord-0dc564e6c7ab48fea61dad3ecff84b79
Source dataset
uspto-grants-1976_09
Patent number
US03980427

Reaction notes

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