4-Trifluoromethyl-benzene sulfochloride → HCID 178484011, compound

HRID 967125Notes

Reaction equation

HRID 967125 reaction equation
[S:1](Cl)([OH:4])(=O)=[O:2].[F:6][C:7]([F:15])([F:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl.[Br:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C@H:23]1[CH2:28][CH2:27][C@H:26]([CH2:29][NH:30][CH3:31])[CH2:25][CH2:24]1>O.O1CCCC1.C(=O)([O-])[O-].[K+].[K+]>[Br:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C@H:23]1[CH2:24][CH2:25][C@H:26]([CH2:29][N:30]([CH3:31])[S:1]([C:11]2[CH:12]=[CH:13][C:8]([C:7]([F:15])([F:14])[F:6])=[CH:9][CH:10]=2)(=[O:4])=[O:2])[CH2:27][CH2:28]1

Participants

6

Reactant 2

HCID 222941704-Trifluoromethyl-benzene sulfochlorideHCID 178484008HCID 178484008, compound

Product 1

HCID 178484011HCID 178484011, compoundYield 92.6%

Reagents, catalysts & solvents 3

HCID 11430Potassium CarbonateCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

0.786 ml Diisopropyl-aethylamine, 0.619 g (2.53 mmol) 4-trifluoromethyl-benzene sulfochloride and 0.952 mg potassium carbonate (dissolved in the minimal amount of water) were added to a solution of 0.718 g (2.30 mmol) trans-[4-(5-bromo-pentyl)-cyclohexylmethyl]-methyl-amine hydrochloride in 15.0 ml of tetrahydrofuran kept at −10° C. The reaction mixture was then intensively stirred for 1 hour at −10° C. and for 1 hour at room temperature. It was subsequently evaporated, poured into 50 ml of an ice/water mixture and extracted 3 times with 50 ml of dichloromethane. The combined dichloromethane phases were dried over magnesium sulfate and evaporated under reduced pressure. The residue formed was chromatographed on silica gel with dichloromethane as the eluent giving 1.03 g (92.6%) trans-N-[4-(5-bromo-pentyl)-cyclohexylmethyl]-N-methyl-4-trifluoromethyl-benzenesulfonamide as colorless amorphous solid, MS: 404 [(M−Br)+].

Workup

  1. customkept at −10° C
  2. customIt was subsequently evaporated
  3. additionpoured into 50 ml of an ice/water mixture
  4. extractionextracted 3 times with 50 ml of dichloromethane
  5. dry with materialThe combined dichloromethane phases were dried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue formed
  8. customwas chromatographed on silica gel with dichloromethane as the eluent

Sources & evidence

ORD record
ord-2664b20a459943dc823c3105e6ba5296
Source dataset
uspto-grants-2005_10
Patent number
US06953806B2

Reaction notes

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