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

HRID 894096Notes

Reaction equation

HRID 894096 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][N:3]1[C:11]([NH:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([NH:25][C:26]([NH2:28])=[O:27])(=[O:24])=[O:23])=[CH:18][CH:17]=1)=[O:12].[CH2:29](N)[CH2:30][CH2:31][CH3:32]>O1CCOCC1>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][N:3]1[C:11]([NH:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([NH:25][C:26]([NH:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:27])(=[O:24])=[O:23])=[CH:18][CH:17]=1)=[O:12]

Participants

4

Reactant 2

HCID 8007ButylamineHCID 705786844-[2-(-1-Oxo-isoindoline-2-carboxamido)ethyl]-benzenesulfonyl-urea

Product 1

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

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4 g of N-(4-[2-(-1-oxo-isoindoline-2-carboxamido)ethyl]-benzenesulfonyl-urea (melting point 207°-209° C., prepared from 4-[2-(1-oxo-isoindoline-2-carboxamido)-ethyl]-benzenesulfonamide and potassium cyanate in 80% ethanol) and 0.73 g of butylamine in 100 ml of dioxane are refluxed for 1 hour. The solvent is then distilled off under reduced pressure, the residue is reprecipitated from very dilute ammonia and recrystallized from dilute acetone. The N-(4-[2-(1-oxo-isoindoline-2-carboxamido)-ethyl]-benzenesulfonyl)-N'-butyl urea obtained melts at 188° to 190° C.

Workup

  1. distillationThe solvent is then distilled off under reduced pressure
  2. customthe residue is reprecipitated from very dilute ammonia
  3. customrecrystallized from dilute acetone

Sources & evidence

ORD record
ord-db1a032d292e415ca0c468f847e11b59
Source dataset
uspto-grants-1981_08
Patent number
US04282239

Reaction notes

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