Benzylsulfamide → HCID 22318901, compound

HRID 497311Notes

Reaction equation

HRID 497311 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N:9]=[C:10]=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2].[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:21])=[O:20])=[CH:15][CH:14]=1>C(Cl)Cl>[CH2:23]([NH:22][S:19]([C:16]1[CH:15]=[CH:14][C:13]([NH:12][C:10]([NH:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=2)=[O:11])=[CH:18][CH:17]=1)(=[O:21])=[O:20])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 66909BenzylsulfamideHCID 27333153-Isocyanatobenzonitrile

Product 1

HCID 22318901HCID 22318901, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-cyanophenylisocyanate (6.4 g, 1 eq) in DCM (100 ml), was added to 4-amino-N-benzylbenzenesulfonamide (10.4 g, 1 eq), dissolved in DCM (100 ml), at 4° C. in small portions, stirred for 1 h. Afterwards the mixture was stirred at rt for 16 h. The solvent was removed in vacuo and the residue was recrystallized from ethanol/water (1/1). The product was filtered, washed 2 times with ethanol/water (1/1) at 4° C., and dried in vacuo to give N-benzyl-4-[3-(3-cyanophenyl)-ureido]-benzenesulfonamide. Yield 90% N-benzyl-4-[3-(3-cyanophenyl)-ureido]-benzenesulfonamide (22 g, 1 eq) was dissolved in ethanol (150 ml). Hydrochloric acid was bubbled through the solution for 2 h at 4° C. Then the solution was stirred for 1 h at rt. The solvent was removed in vacuo. The product was washed with ethanol/water (1/1) at 4° C., and dried in vacuo to give 3-[3-(4-benzylsulfamoylphenyl)-ureido]-benzimidic acid ethyl ester. Yield 75%.

Workup

  1. stirringAfterwards the mixture was stirred at rt for 16 h
  2. customThe solvent was removed in vacuo
  3. customthe residue was recrystallized from ethanol/water (1/1)
  4. filtrationThe product was filtered
  5. washwashed 2 times with ethanol/water (1/1) at 4° C.
  6. customdried in vacuo

Sources & evidence

ORD record
ord-637c8bf5171e419ba8fdb0f068e81ba3
Source dataset
uspto-grants-2005_09
Patent number
US06949567B2

Reaction notes

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