Hydrochloric Acid → 2-(Oxan-4-ylmethoxy)-5-sulfamoylbenzamide

HRID 2167966Notes

Reaction equation

HRID 2167966 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([S:17]([NH2:20])(=[O:19])=[O:18])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)#[N:2].[OH:21]O.[OH-].[Na+].Cl>C(O)C.O1CCCC1.ClCCl>[S:17]([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH2:10][CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[C:3]([CH:4]=1)[C:1]([NH2:2])=[O:21])(=[O:19])(=[O:18])[NH2:20]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 671264133-cyano-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamide

Product 1

HCID 671264652-(Oxan-4-ylmethoxy)-5-sulfamoylbenzamide

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
35 °C

Procedure

To a solution of EXAMPLE 38A (0.455 g) in ethanol (3 mL) and tetrahydrofuran (1 mL) was added hydrogen peroxide (30% in water, 2 mL) followed by 1 N aqueous NaOH (1.024 ml) and heated to 35° C. for 3 hours. The reaction was poured into dichloromethane (50 mL) and 1N aqueous HCl (25 mL). The aqueous layer was extracted with dichloromethane (3×50 mL). The precipitate contained in the combined organic layers was collected by filtration to give the title compound.

Workup

  1. extractionThe aqueous layer was extracted with dichloromethane (3×50 mL)
  2. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-93ebafc999e2444e9f08b00a31e4171e
Source dataset
uspto-grants-2015_06
Patent number
US09045475B2

Reaction notes

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