Butanethiol → HCID 87870791, compound

HRID 1351055Notes

Reaction equation

HRID 1351055 reaction equation
[F:1][C:2]([F:8])([F:7])[S:3]([O-:6])(=[O:5])=[O:4].F[C:10]1[CH:15]=[CH:14][C:13]([S+:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:12][CH:11]=1.[OH-].[Na+].[CH2:31]([SH:35])[CH2:32][CH2:33][CH3:34]>ClCCl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:1][C:2]([F:8])([F:7])[S:3]([O-:6])(=[O:5])=[O:4].[CH2:31]([S:35][C:10]1[CH:15]=[CH:14][C:13]([S+:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)[CH2:32][CH2:33][CH3:34]

Participants

6

Reactant 3

HCID 8012ButanethiolHCID 14798Sodium HydroxideHCID 16213837(4-Fluorophenyl)(diphenyl)sulfanium trifluoromethanesulfonate

Product 1

HCID 87870791HCID 87870791, compoundYield 57.3%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Procedure

26.7 g of 4-fluorophenyl diphenylsulfonium trifluoromethanesulfonate was dissolved in 200 g of dichloromethane in a reaction flask, in which the atmosphere was replaced with nitrogen. 200 g of 10 wt % sodium hydroxide aqueous solution, 5.8 g of tetra-n-butylammonium bromide, and 6.71 g of n-butanethiol were added. The mixture was stirred for 30 minutes at room temperature and transferred to a separatory funnel, shaken, and allowed to stand still. The water layer was removed. After the addition of 300 ml of distilled water, the mixture was shaken and allowed to stand still. The water layer was removed. The resulting dichloromethane solution was dried with anhydrous magnesium sulfate, filtered, and dried using an evaporator. After evaporating dichloromethane from the dried solution, the residual liquid was dried under reduced pressure to obtain 17.8 g of 4-n-butylthiophenyl diphenylsulfonium trifluoromethanesulfonate.

Workup

  1. customtransferred to a separatory funnel
  2. stirringshaken
  3. customThe water layer was removed
  4. additionAfter the addition of 300 ml of distilled water
  5. stirringthe mixture was shaken
  6. customThe water layer was removed
  7. dry with materialThe resulting dichloromethane solution was dried with anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customdried
  10. customan evaporator
  11. customAfter evaporating dichloromethane from the dried solution
  12. customthe residual liquid was dried under reduced pressure

Sources & evidence

ORD record
ord-6991987230394638a63283bdebfc4826
Source dataset
uspto-grants-2007_05
Patent number
US07217492B2

Reaction notes

Loading…