Butanethiol → HCID 21097673, compound

HRID 1351057Notes

Reaction equation

HRID 1351057 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:24]2[CH:29]=[CH:28][C:27](F)=[CH:26][CH:25]=2)[C:17]2[CH:22]=[CH:21][C:20](F)=[CH:19][CH:18]=2)=[CH:12][CH:11]=1.[OH-].[Na+].[CH2:33]([SH:37])[CH2:34][CH2:35][CH3:36]>ClCCl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:1][C:2]([F:8])([F:7])[S:3]([O-:6])(=[O:5])=[O:4].[CH2:33]([S:37][C:10]1[CH:15]=[CH:14][C:13]([S+:16]([C:24]2[CH:29]=[CH:28][C:27]([S:3][CH2:2][CH2:18][CH2:17][CH3:22])=[CH:26][CH:25]=2)[C:17]2[CH:22]=[CH:21][C:20]([S:16][CH2:13][CH2:12][CH2:11][CH3:10])=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)[CH2:34][CH2:35][CH3:36]

Participants

6

Reactant 3

HCID 8012ButanethiolHCID 14798Sodium HydroxideHCID 23021335HCID 23021335, compound

Product 1

HCID 21097673HCID 21097673, compoundYield 120.8%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Procedure

26.7 g of tris(4-fluorophenyl)sulfonium trifluoromethanesulfonate was dissolved in 200 g of dichloromethane in a reaction flask, in which the atmosphere was replaced with nitrogen. 600 g of 10 wt % sodium hydroxide aqueous solution, 5.8 g of tetra-n-butylammonium bromide, and 20.1 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 dichloromethane solution was dried with anhydrous magnesium sulfate and filtered. After evaporating dichloromethane from the dried solution, the residual liquid was dried under reduced pressure to obtain 23.4 g of tris(4-n-butylthiophenyl)sulfonium 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 dichloromethane solution was dried with anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customAfter evaporating dichloromethane from the dried solution
  10. customthe residual liquid was dried under reduced pressure

Sources & evidence

ORD record
ord-300e9bdcb7c34c67839e90a34cbf56e3
Source dataset
uspto-grants-2007_05
Patent number
US07217492B2

Reaction notes

Loading…