Toluene → HCID 11687518, compound

HRID 2253035Notes

Reaction equation

HRID 2253035 reaction equation
Cl[CH2:2][C@H:3]([OH:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[C:7]([Cl:13])[CH:6]=1.[OH-].[Na+].S(O)(O[CH2:21][CH2:22][NH2:23])(=O)=O.C1(C)C=CC=CC=1>CO.O>[Cl:13][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][C:8]=1[S:11][CH3:12])[CH2:4][C@H:3]1[O:14][CH2:21][CH2:22][NH:23][CH2:2]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 14798Sodium Hydroxide2×HCID 70223Aminoethyl sulfateHCID 67073079HCID 67073079, compound

Product 1

HCID 11687518HCID 11687518, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

The solution of 0.4 g (1.6 mmol) (R)-1-chloro-3-(3-chloro-4-methylsulfanyl-phenyl)-propan-2-ol in 1.4 mL methanol was treated with a solution of 0.39 g (1.0 mmol) sodium hydroxide in 0.7 mL water and 0.92 g (6.5 mmol) 2-aminoethyl hydrogen sulfate. The reaction was warmed to 45° C. and stirred for 2.5 h. After the addition of 0.42 g (10.5 mmol) solid sodium hydroxide and 7 mL toluene the reaction temperature was raised to 65° C. After 4 h the reaction mixture was poured on water and extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue was chromatographed using MPLC and dichloromethane: methanol: ammonia (9:1:0.1 v/v) as eluant to give the compound as a light brown oil (38%).

Workup

  1. temperaturewas raised to 65° C
  2. additionAfter 4 h the reaction mixture was poured on water
  3. extractionextracted three times with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was chromatographed

Sources & evidence

ORD record
ord-6d9c8c62ee0349148e2c9c386b07f9ca
Source dataset
uspto-grants-2008_01
Patent number
US07323466B2

Reaction notes

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