Tert-Butylamine → 3-(tert-butylsulfamoyl)-4-chlorobenzoic acid

HRID 461172Notes

Reaction equation

HRID 461172 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[Cl:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]=1[S:16](Cl)(=[O:18])=[O:17]>C(O)C>[C:1]([NH:5][S:16]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][C:7]=1[Cl:6])[C:11]([OH:13])=[O:12])(=[O:17])=[O:18])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 756134-Chloro-3-(chlorosulphonyl)benzoic acid

Product 1

HCID 23938783-(tert-butylsulfamoyl)-4-chlorobenzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
30 °C

Procedure

To a mixture of 36.5 g (0.5 mol) of tert.-butylamine and 250 ml of ethanol were added 25.5 g (0.1 mol) of 4-chloro-3-chlorosulfonylbenzoic acid in small portions while stirring and cooling, the reaction temperature being maintained at about 30° C. After a dwelling time over night at room temperature, the solvent was distilled off, the residue was dissolved in about 200 ml of water, the pH was adjusted to 1 with concentrated HCl and the crystals were filtered off. Melting point: 250° C.

Workup

  1. temperaturecooling
  2. waitAfter a dwelling time over night at room temperature
  3. distillationthe solvent was distilled off
  4. dissolutionthe residue was dissolved in about 200 ml of water
  5. filtrationthe crystals were filtered off

Sources & evidence

ORD record
ord-9238b6692c214bc99dc8d0a44ec7240c
Source dataset
uspto-grants-1977_12
Patent number
US04061761

Reaction notes

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