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

HRID 1437539Notes

Reaction equation

HRID 1437539 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 uL 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-31f2d209f34b409eb96694dff6bce75d
Source dataset
uspto-grants-2009_11
Patent number
US07622474B2

Reaction notes

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