Hydrochloric Acid → N-(4-[2-(1-oxo-isoindoline-2-carboxamido)-ethyl]-benzenesulfonyl)-N'-butyl-urea

HRID 894094Notes

Reaction equation

HRID 894094 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]([NH:16][CH2:17][CH2:18][CH2:19][CH3:20])=[O:15])(=[O:12])=[O:11])=[CH:6][CH:5]=1.[OH-].[Na+].[O:23]=[C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:26][N:25]1[C:33](Cl)=[O:34].Cl>O.CC(C)=O>[O:23]=[C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:26][N:25]1[C:33]([NH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]([NH:16][CH2:17][CH2:18][CH2:19][CH3:20])=[O:15])(=[O:12])=[O:11])=[CH:6][CH:5]=1)=[O:34]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12795528N-(4-[2-amino-ethyl]-benzenesulfonyl)-N'-butyl-ureaHCID 129283901,3-Dihydro-1-oxo-2H-isoindole-2-carbonyl chloride

Product 1

HCID 21162325N-(4-[2-(1-oxo-isoindoline-2-carboxamido)-ethyl]-benzenesulfonyl)-N'-butyl-urea

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

3 g of N-(4-[2-amino-ethyl]-benzenesulfonyl)-N'-butyl-urea (melting point 210°-212° C., prepared by saponification of N-(4-[2-acetylamino-ethyl]-benzenesulfonyl)-N'-butyl-urea with sodium hydroxide solution) are dissolved with 0.4 g of sodium hydroxide in 50 ml of water and 50 ml of acetone and, while stirring, a solution of 2 g of 1-oxo-isoindoline-2-carboxylic acid chloride (melting point 119°-121° C., prepared from 1-oxo-isoindoline sodium and phosgene) in about 50 ml of acetone is added. The temperature of the mixture increases slightly. Stirring is continued for 2 hours at room temperature, whereupon the residue is acidified with dilute hydrochloric acid. The precipitate is reprecipitated from dilute ammonia and recrystallized from dilute acetone. The N-(4-[2-(1-oxo-isoindoline-2-carboxamido)-ethyl]-benzenesulfonyl)-N'-butyl-urea melts at 188°-190° C.

Workup

  1. temperatureThe temperature of the mixture increases slightly
  2. stirringStirring
  3. customThe precipitate is reprecipitated from dilute ammonia
  4. customrecrystallized from dilute acetone

Sources & evidence

ORD record
ord-fcc0b3feb59546149b9f61e56cdfb752
Source dataset
uspto-grants-1981_08
Patent number
US04282239

Reaction notes

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