Potassium Hydroxide → 4-Benzyl-3-n-butoxy-5-sulfamylbenzoic acid

HRID 328966Notes

Reaction equation

[C:1]([C:9]1[C:17]([S:18](=[O:21])(=[O:20])[NH2:19])=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]=1[O:22][CH2:23][CH2:24][CH2:25][CH3:26])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN.[OH-].[K+]>O.C(O)COCCO>[CH2:1]([C:9]1[C:17]([S:18](=[O:21])(=[O:20])[NH2:19])=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]=1[O:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 4-benzoyl-3-n-butoxy-5-sulfamylbenzoic acid (0.94 g), 98% aqueous hydrazine hydrate (1.5 ml), potassium hydroxide (0.5 g) in water (1.0 ml) and diethylene glycol (6.5 ml) is stirred at about 130° C. for 3 hours. The temperature is then slowly raised to 215° C. allowing volatile material to distil off. The stirring at 215° C. is continued for a further 2-3 hours until the nitrogen evolution has ceased. After cooling and dilution with water (10 ml), the resulting solution is acidified with conc. hydrochloric acid (1 ml). The resulting precipitate is collected by filtration and washed with water. After drying and recrystallization twice from aqueous ethanol, 4-benzyl-3-n-butoxy-5-sulfamylbenzoic acid is obtained with a melting point of 228°-229° C.

Workup

temperatureThe temperature is then slowly raised to 215° C.
customto distil off
waitThe stirring at 215° C. is continued for a further 2-3 hours until the nitrogen evolution
temperatureAfter cooling
filtrationThe resulting precipitate is collected by filtration
washwashed with water
customAfter drying
customrecrystallization twice from aqueous ethanol

Sources & evidence

ORD record: ord-5f8ae46e8e964b16821ab7255bda57cf
Source dataset: uspto-grants-1977_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04018794

Reaction notes

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