Water → {[4-(5-Chloro-1,3-dioxobenzo [c]azolidin-2-yl)-3-methylphenyl]amino}-n-(phenylsulfonimidoyl)carboxamide

HRID 1071721Notes

Reaction equation

HRID 1071721 reaction equation
[Cl:1][C:2]1[CH:41]=[CH:40][C:5]2[C:6](=[O:39])[N:7]([C:10]3[CH:15]=[CH:14][C:13]([NH:16][C:17]([NH:19][S:20]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)(=[N:22]CC4C=CC(OC)=CC=4)=[O:21])=[O:18])=[CH:12][C:11]=3[CH3:38])[C:8](=[O:9])[C:4]=2[CH:3]=1.O.[N+]([O-])([O-])=O.[NH4+]>O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+]>[Cl:1][C:2]1[CH:41]=[CH:40][C:5]2[C:6](=[O:39])[N:7]([C:10]3[CH:15]=[CH:14][C:13]([NH:16][C:17]([NH:19][S:20]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)(=[NH:22])=[O:21])=[O:18])=[CH:12][C:11]=3[CH3:38])[C:8](=[O:9])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 22985Ammonium nitrateHCID 20799232{[4-(5-Chloro-1,3-dioxobenzo[c]azolidin-2-yl)-3-methylphenyl]-amino}-n-(n-p-methoxybenzylphenylsulfonimidoyl)carboxamide

Product 1

HCID 20799234{[4-(5-Chloro-1,3-dioxobenzo [c]azolidin-2-yl)-3-methylphenyl]amino}-n-(phenylsulfonimidoyl)carboxamide

Reagents, catalysts & solvents 1

HCID 180504Ceric ammonium nitrateSolvent

Procedure

To 10 mg (0.016 mmol) of {[4-(5-chloro-1,3-dioxobenzo[c]azolidin-2-yl)-3-methylphenyl]-amino}-N-(N-p-methoxybenzylphenylsulfonimidoyl)carboxamide dissolved in 380 μL of CAN followed by 96 μL of water was added 70 mg (0.13 mmol) of cerric ammonium nitrate. After 20 m, the reaction was complete and purified by RP-HPLC to give 1.8 mg (23%) after lyophilization. ES-MS (M+H)+=469 (Cl).

Workup

  1. custompurified by RP-HPLC
  2. customto give 1.8 mg (23%) after lyophilization

Sources & evidence

ORD record
ord-7a3b36c765354a3c874ec19fe6ece38c
Source dataset
uspto-grants-2005_06
Patent number
US06906063B2

Reaction notes

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