p-Toluenesulfonic acid → HCID 86742758, compound

HRID 1382655Notes

Reaction equation

HRID 1382655 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8](/[C:11](/[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:12](\[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)/[C:13]([F:16])([F:15])[F:14])=[CH:7][CH:6]=1.[CH2:29]([NH2:35])[CH2:30][CH2:31][CH2:32][CH2:33][CH3:34].[C:36]1([CH3:46])[CH:41]=[CH:40][C:39]([S:42]([OH:45])(=[O:44])=[O:43])=[CH:38][CH:37]=1>COCCO.C(O)(C)C>[S:42]([C:39]1[CH:40]=[CH:41][C:36]([CH3:46])=[CH:37][CH:38]=1)([OH:45])(=[O:44])=[O:43].[C:23]1(/[C:11](/[C:8]2[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][NH:35][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:6][CH:7]=2)=[C:12](/[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)\[C:13]([F:16])([F:15])[F:14])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8102HexylamineHCID 13292770HCID 13292770, compound

Product 1

HCID 86742758HCID 86742758, compoundYield 91.8%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 80192-MethoxyethanolSolvent

Procedure

2.23 g (5 mmoles) of (E)-1-[4-(2-bromoethoxy)-phenyl]-1,2-diphenyl-3,3,3-trifluoro-propene, prepared as described in Example 7, are dissolved in a mixture of 5.0 g (50 mmoles) of n-hexylamine and 10 ml of 2-methoxyethanol. The mixture is boiled for 30 minutes, then evaporated, and the residue is passed through a chromatographic column filled with 50 g of silica gel. The column is eluted with benzene. The fractions which are chromatographically uniform are combined and evaporated, the residue is dissolved in 5 ml of isopropanol, and a solution of 1.20 g (6 mmoles) of p-toluenesulfonic acid in 6 ml of isopropanol is added. The separated crystals are filtered off and washed with ether. 2.14 g (91.8%) of the aimed compound are obtained; m.p.: 151°-153° C.

Workup

  1. customevaporated
  2. additionfilled with 50 g of silica gel
  3. washThe column is eluted with benzene
  4. customevaporated
  5. dissolutionthe residue is dissolved in 5 ml of isopropanol
  6. filtrationThe separated crystals are filtered off
  7. washwashed with ether

Sources & evidence

ORD record
ord-2a3a99eae1054ac5ae25fd792649371f
Source dataset
uspto-grants-1989_02
Patent number
US04806685

Reaction notes

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