Hydrochloric Acid → HCID 11687661, compound

HRID 1350834Notes

Reaction equation

HRID 1350834 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][C:3]=1[NH:10][S:11]([CH3:14])(=[O:13])=[O:12].O1CCCC1.Cl>CO.[Pd]>[ClH:1].[NH2:9][CH2:8][C:6]1[CH:5]=[CH:4][C:3]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])=[C:2]([Cl:1])[CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 11615562HCID 11615562, compound

Product 1

HCID 11687661HCID 11687661, compoundYield 167.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of N-(2-chloro-4-cyanophenyl)methanesulfonamide (0.5 g, 2.2 mmol) and 10% Pd—C (100 mg) in methanol (7.5 ml)-tetrahydrofuran (7.5 ml)-12M aqueous solution of hydrogen chloride (3.0 ml) was stirred under H2 balloon pressure for 2 hours at ambient temperature. Then, filtration to remove 10% Pd—C, evaporation gave the crude residue, which was applied to recrystallization from methanol and diisopropylether to furnish 500 mg (85% yield) of title compound as a white solid.

Workup

  1. filtrationThen, filtration
  2. customto remove
  3. custom10% Pd—C, evaporation
  4. customgave the crude residue, which
  5. customwas applied to recrystallization from methanol and diisopropylether

Sources & evidence

ORD record
ord-04637321a0b342b69a133f43286417bf
Source dataset
uspto-grants-2007_05
Patent number
US07214824B2

Reaction notes

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