HCID 22601342, compound → HCID 22601393, compound

HRID 970900Notes

Reaction equation

HRID 970900 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([S:9]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1>CO.C(Cl)Cl.O=[Mn]=O>[CH:2]([C:3]1[CH:4]=[C:5]([S:9]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1)=[O:1]

Participants

5

Reactant 1

HCID 22601342HCID 22601342, compound

Product 1

HCID 22601393HCID 22601393, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 14801Manganese dioxideCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

3-Hydroxymethyl-N-pyridin-2-ylmethyl-benzenesulfonamide (crude from previous step, 2.87 mmol) and MnO2 (2.9 g, 28.7 mmol) in methanol (0.5 mL) and CH2Cl2 (15 mL) were reacted at 50° C. under N2 overnight. The mixture was concentrated and purified by chromatography on silica gel (50% ethyl acetate and CH2Cl2) to afford the title compound (600 mg, 79% over two steps) as a white foam.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by chromatography on silica gel (50% ethyl acetate and CH2Cl2)

Sources & evidence

ORD record
ord-a25ff7aca925404694c810a1bd21de08
Source dataset
uspto-grants-2007_12
Patent number
US07312234B2

Reaction notes

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