Methyl triflate → HCID 86742070, compound

HRID 570022Notes

Reaction equation

HRID 570022 reaction equation
[C:1]1([CH3:24])[CH:6]=[CH:5][C:4]([S:7]([N:10]=[S:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[F:25][C:26]([F:33])([F:32])[S:27]([O:30]C)(=[O:29])=[O:28]>C1(C)C=CC=CC=1>[F:25][C:26]([F:33])([F:32])[S:27]([O-:30])(=[O:29])=[O:28].[C:1]1([CH3:24])[CH:2]=[CH:3][C:4]([S:7]([N:10]([S+:11]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH3:26])(=[O:8])=[O:9])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 9526Methyl triflateHCID 264695N-(Diphenyl-lambda~4~-sulfanylidene)-4-methylbenzene-1-sulfonamide

Product 1

HCID 86742070HCID 86742070, compoundYield 105.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

10.65 g (0.03 mol) of N-p-toluenesulfonyldiphenylsulfilimine were suspended in 50 ml of dry toluene and, after addition of 6.55 g (0.04 mol) of methyl trifluoromethanesulfonate, were stirred under reflux for 2 hours. On cooling, the reaction solution divided into two phases, the lower of which was removed. The solid residue remaining on concentrating the lower phase was recrystallized from ethyl acetate and dried to give 11.0 g of the salt (I). Analysis and properties are indicated in Table 1.

Workup

  1. temperatureunder reflux for 2 hours
  2. temperatureOn cooling
  3. customthe lower of which was removed
  4. concentrationon concentrating the lower phase
  5. customwas recrystallized from ethyl acetate
  6. customdried

Sources & evidence

ORD record
ord-6010e824a3964624a433eeb4a8df728f
Source dataset
uspto-grants-1988_03
Patent number
US04734444

Reaction notes

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