Hydrochloric Acid → n-{[4-(1,3-Dioxobenzo[c]azolidin-2-yl)phenyl]sulfonyl}(phenylamino)carboxamide

HRID 562667Notes

Reaction equation

HRID 562667 reaction equation
[O:1]=[C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4](=[O:11])[N:3]1[C:12]1[CH:17]=[CH:16][C:15]([S:18]([NH2:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1.[CH2:22]1[CH2:32][CH2:31][N:30]2[C:25](=NCC[CH2:29]2)[CH2:24][CH2:23]1.C1(S(N=C=O)(=O)=[O:40])C=CC=CC=1.Cl>CS(C)=O>[O:11]=[C:4]1[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:2](=[O:1])[N:3]1[C:12]1[CH:17]=[CH:16][C:15]([S:18]([NH:21][C:29]([NH:30][C:25]2[CH:24]=[CH:23][CH:22]=[CH:32][CH:31]=2)=[O:40])(=[O:19])=[O:20])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 76096Phenylsulphonyl isocyanateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 35864944-(1,3-Dioxo-1,3-dihydro-isoindol-2-YL)-benzenesulfonamide

Product 1

HCID 22064432n-{[4-(1,3-Dioxobenzo[c]azolidin-2-yl)phenyl]sulfonyl}(phenylamino)carboxamideYield 100%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 4-(1,3-dioxobenzo[c]azolidin-2-yl)benzenesulfonamide in 660 uL of DMSO was added 60 mg (0.40 mmol) of DBU followed by 36 μl (0.33 mmol) of phenylsulfonylisocyanate. After stirring for 0.5 h, the mixture was poured into 1N HCl, cooled, and the precipitate was collected by filtration and dried under vacuum to give 137 mg (100%) of the titled compound.

Workup

  1. temperaturecooled
  2. filtrationthe precipitate was collected by filtration
  3. customdried under vacuum

Sources & evidence

ORD record
ord-9852f38b1e2945c9aea84b13399fbe52
Source dataset
uspto-grants-2011_11
Patent number
US08067428B2

Reaction notes

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