Water → n-Butyl 3-n-butylamino-4-phenyl-5-sulfamylbenzoate

HRID 1605577Notes

Reaction equation

HRID 1605577 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:17](=[O:20])(=[O:19])[NH2:18])[C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]([OH:7])=[O:6].[CH2:21](I)[CH2:22][CH2:23][CH3:24].O>C(O)CCC>[CH2:21]([NH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:17](=[O:20])(=[O:19])[NH2:18])[C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]([O:7][CH2:3][CH2:2][CH2:10][CH3:9])=[O:6])[CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 962WaterHCID 10962Butyl iodideHCID 215468413-Amino-4-phenyl-5-sulfamylbenzoic acid

Product 1

HCID 53834574n-Butyl 3-n-butylamino-4-phenyl-5-sulfamylbenzoate

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 3-amino-4-phenyl-5-sulfamylbenzoic acid (1.46 g) and n-butyl iodide (1.5 ml) in n-butanol (20 ml) is refluxed for 3-4 days under such conditions, that the water formed during the reaction is separated. After 12, 24, 36 and 48 hours, additional amounts of n-butyl iodide (each time 0.75 ml) are added. The resulting solution is evaporated in vacuo, and the obtained crude n-butyl 3-n-butylamino-4-phenyl-5-sulfamylbenzoate is saponified by heating with 2 N sodium hydroxide (20 ml) for 30 minutes. After cooling, the resulting solution is acidified with 4 N hydrochloric acid (12 ml) to precipitate 3-n-butylamino-4-phenyl-5-sulfamylbenzoic acid, which is collected by filtration, washed with water and dried. After recrystallization from aqueous ethanol, the acid is obtained with a melting point of 134°-136° C.

Workup

  1. customformed during the reaction
  2. customis separated
  3. additionAfter 12, 24, 36 and 48 hours, additional amounts of n-butyl iodide (each time 0.75 ml) are added
  4. customThe resulting solution is evaporated in vacuo

Sources & evidence

ORD record
ord-4a8cff9b3960437e96ff2050c91b829d
Source dataset
uspto-grants-1976_04
Patent number
US03950380

Reaction notes

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