Hydrochloric Acid → 5-Chloro-2-methoxy-N-(2-(1-(3-isopropylureidosulfonyl)piperidin-4-yl)ethyl)benzamide

HRID 2043081Notes

Reaction equation

HRID 2043081 reaction equation
OO.[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([O:31][CH3:32])=[C:8]([CH:30]=1)[C:9]([NH:11][CH2:12][CH2:13][CH:14]1[CH2:19][CH2:18][N:17]([S:20]([NH:23][C:24]([NH:26][CH:27]([CH3:29])[CH3:28])=S)(=[O:22])=[O:21])[CH2:16][CH2:15]1)=[O:10].S([O-])([O-])=[O:34].[Na+].[Na+].Cl>[OH-].[Na+]>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([O:31][CH3:32])=[C:8]([CH:30]=1)[C:9]([NH:11][CH2:12][CH2:13][CH:14]1[CH2:19][CH2:18][N:17]([S:20]([NH:23][C:24]([NH:26][CH:27]([CH3:29])[CH3:28])=[O:34])(=[O:22])=[O:21])[CH2:16][CH2:15]1)=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 24437Sodium SulfiteHCID 115185565-Chloro-2-methoxy-N-(2-(1-(3-isopropylthioureidosulfonyl)piperidin-4-yl)ethyl)benzamide

Product 1

HCID 596607085-Chloro-2-methoxy-N-(2-(1-(3-isopropylureidosulfonyl)piperidin-4-yl)ethyl)benzamideYield 45.6%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

0.1 ml (1.16 mmol) of 30% strength hydrogen peroxide solution was added to a solution of 48 mg (0.1 mmol) of 5-chloro-2-methoxy-N-(2-(1-(3-isopropylthioureidosulfonyl)piperidin-4-yl)ethyl)benzamide in 2 ml of 0.5 M sodium hydroxide solution at 0° C. After the reaction mixture had been kept at 0° C. for 2 hours, 100 mg of sodium sulfite were added, and the mixture was acidified by means of 2 M hydrochloric acid. The precipitated solid was filtered off, washed with water until neutral and recrystallized from diethyl ether. 21 mg (45%) of the title compound were obtained as a colorless solid.

Workup

  1. filtrationThe precipitated solid was filtered off
  2. washwashed with water until neutral and
  3. customrecrystallized from diethyl ether

Sources & evidence

ORD record
ord-c5d38b2426d34f3a80d03774077a205c
Source dataset
uspto-grants-2013_11
Patent number
US08586612B2

Reaction notes

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