Chloroform methanol → N-[(4-Formylphenyl)methyl]methanesulfonamide

HRID 1387646Notes

Reaction equation

HRID 1387646 reaction equation
[CH3:1][S:2]([NH:5][CH2:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11][OH:12])=[CH:9][CH:8]=1)(=[O:4])=[O:3].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.CO.C(Cl)(Cl)Cl>C(Cl)Cl>[CH3:1][S:2]([NH:5][CH2:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][CH:8]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 21584188Chloroform methanolHCID 53642941HCID 53642941, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 18771481N-[(4-Formylphenyl)methyl]methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[(methanesulfonamido)methyl]benzyl alcohol (1.0 g, 4.6 mmol) in CH2Cl2 (25 mL) was added pyridinium chlorochromate (1.5 g, 7.0 mmol). The reaction mixture was stirred for 1 h at rt and poured through a pad of silica gel eluting with 2% MeOH/CHCl3. The title compound was isolated as a tan solid (1.0 g, 100%): 1H NMR (CDCl3): d 10.03 (s,1H); 7.88 (d, 2H); 7.57 (d, 2H); 4.79 (br s, 1H); 4.43 (d, 2H); 2.93 (s, 3H).

Sources & evidence

ORD record
ord-7353823873f642c2a496e291d92e8a38
Source dataset
uspto-grants-2001_07
Patent number
US06268370B1

Reaction notes

Loading…