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

HRID 894093Notes

Reaction equation

HRID 894093 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]([OH:24])=[O:23])=[CH:18][CH:17]=1)=[O:12].S(Cl)(O)(=O)=O.S([O-])([O-])=O.[Na+].[Na+].O[NH:37][C:38]([NH:40][CH2:41][CH2:42][CH2:43][CH3:44])=[O:39].S(Cl)(Cl)=O.N>O1CCOCC1.O>[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:17]=[CH:18][C:19]([S:22]([NH:37][C:38]([NH:40][CH2:41][CH2:42][CH2:43][CH3:44])=[O:39])(=[O:24])=[O:23])=[CH:20][CH:21]=1)=[O:12]

Participants

9

Reactant 6

HCID 222AmmoniaHCID 24386Thionyl ChlorideHCID 24437Sodium SulfiteHCID 24638Chlorosulfonic acidHCID 79761N-Butyl-N'-hydroxyureaHCID 211623984-[2-(1-Oxo-isoindoline-2-carboxamido)-ethyl]-benzenesulfinic acid

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

3.4 g of 4-[2-(1-oxo-isoindoline-2-carboxamido)-ethyl]-benzenesulfinic acid (crude product, prepared by reduction of the sulfochloride with sodium sulfite) and 1.4 g of N-hydroxy-N'-butyl-urea are suspended in 40 ml of dioxane and a solution of 1 ml of thionyl chloride in 10 ml of dioxane is added dropwise while stirring. The mixture is then heated for 2 hours to 60° C., whereby a limpid solution is formed. The solution is poured into water, the precipitated substance is treated with dilute ammonia, filtered, acidified and the reaction product is recrystallized from dilute acetone. The N-(4-[2-(1-oxo-isoindoline-2-carboxamido)-ethyl]-benzenesulfonyl)-N'-butyl-urea obtained melts at 188°-190° C.

Workup

  1. temperatureThe mixture is then heated for 2 hours to 60° C., whereby a limpid solution
  2. customis formed
  3. filtrationfiltered
  4. customthe reaction product is recrystallized from dilute acetone

Sources & evidence

ORD record
ord-2a951a18b4854d6ea0a8d51dfe41047f
Source dataset
uspto-grants-1981_08
Patent number
US04282239

Reaction notes

Loading…