Butylamine → 5-n-Butylsulphamyl-4-chloro-3-nitro-benzoic acid

HRID 1730433Notes

Reaction equation

HRID 1730433 reaction equation
[CH2:1]([NH2:5])[CH2:2][CH2:3][CH3:4].[OH-].[Na+].[Cl:8][C:9]1[C:17]([S:18](Cl)(=[O:20])=[O:19])=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]=1[N+:22]([O-:24])=[O:23]>O>[Cl:8][C:9]1[C:17]([S:18](=[O:19])(=[O:20])[NH:5][CH2:1][CH2:2][CH2:3][CH3:4])=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]=1[N+:22]([O-:24])=[O:23]

Participants

5

Reactant 3

HCID 8007ButylamineHCID 14798Sodium HydroxideHCID 898924-Chloro-5-chlorosulfonyl-3-nitrobenzoic acid

Product 1

HCID 215060165-n-Butylsulphamyl-4-chloro-3-nitro-benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The starting material is prepared as follows: To the stirred solution 7.3 gof n-butylamine, 8 g of sodium hydroxide in 200 ml of water, 30 g of 4-chloro-5-chlorosulfonyl-3-nitrobenzoic acid are added portionwise while keeping the temperature between 0° and 5°. After 1/2 hour the mixture is allowed to warm to room temperature for 2 hours. The supernatant solution is filtered, the filtrate combined with 25 ml of 2N of hydrochloric acid, the precipitate formed collected and recrystallized from aqueous ethanol, to yield the 4-chloro-3-nitro-5-n-butylsulfamoylbenzoic acid melting at 199°-201°.

Workup

  1. customThe starting material is prepared
  2. customthe temperature between 0° and 5°
  3. filtrationThe supernatant solution is filtered
  4. customthe precipitate formed
  5. customcollected
  6. customrecrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-6bbe77f414554f17ad09d00900e43526
Source dataset
uspto-grants-1976_11
Patent number
US03992440

Reaction notes

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