Diazomethane → HCID 53984498, compound

HRID 368561Notes

Reaction equation

HRID 368561 reaction equation
[N+](=[CH2:3])=[N-].[C:4]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][C:15]([CH2:17][C:18]([NH:21][S:22]([C:25]([F:28])([F:27])[F:26])(=[O:24])=[O:23])([CH3:20])[CH3:19])=[O:16])([CH3:7])([CH3:6])[CH3:5]>CCOCC>[CH3:3][N:21]([C:18]([CH3:20])([CH3:19])[CH2:17][C:15]([O:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:4]([CH3:5])([CH3:6])[CH3:7])=[O:16])[S:22]([C:25]([F:28])([F:26])[F:27])(=[O:24])=[O:23]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 21195227HCID 21195227, compound

Product 1

HCID 53984498HCID 53984498, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A freshly prepared solution of diazomethane in anhydrous ether was added in excess to a solution of N-[2-(2-tert-butylphenylcarboxy)-1,1-dimethylethyl]trifluoromethanesulfonamide (13.1 g) in ether. The resulting yellow solution was allowed to stand at RT overnight, then was washed with 10% HCl followed by 2.5N aq NaOH. The organic solution was dried (MgSO4), and concentrated to afford 13.0 g of pure N-methyl-N-[2-(2-tert-butylphenylcarboxy)-1,1-dimethylethyl]trifluoromethanesulfonamide as a white solid, a 96% yield. m.p. 42-44° C.

Workup

  1. washwas washed with 10% HCl
  2. dry with materialThe organic solution was dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3642fd97a6d84408bd09a17d77b61dcd
Source dataset
uspto-grants-2000_10
Patent number
US06133252

Reaction notes

Loading…