Hydrochloric Acid → HCID 178447986, compound

HRID 1443611Notes

Reaction equation

HRID 1443611 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].ClCCl.[CH2:9]([C@H:12]1[CH2:17][CH2:16][C@H:15]([CH2:18][CH2:19][C@H:20]2[CH2:25][CH2:24][C@H:23]([CH2:26][OH:27])[CH2:22][CH2:21]2)[CH2:14][CH2:13]1)[CH2:10][CH3:11].Cl>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[CH3:1][S:2]([O:27][CH2:26][C@H:23]1[CH2:22][CH2:21][C@H:20]([CH2:19][CH2:18][C@H:15]2[CH2:16][CH2:17][C@H:12]([CH2:9][CH2:10][CH3:11])[CH2:13][CH2:14]2)[CH2:25][CH2:24]1)(=[O:4])=[O:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 178447983HCID 178447983, compound

Product 1

HCID 178447986HCID 178447986, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

Methanesulfonyl chloride (15.0 mL) was added by titration under water-cooling conditions to dichloromethane solution (200 mL) of trans-4-(2-(trans-4-propylcyclohexyl)ethyl)cyclohexyl methanol (47.3 g), and then pyridine (17.0 mL) was also added by titration, with the temperature maintained. After being cooled down to room temperature, 4-(N,N-dimethylamino)pyridine (2.6 g) was added, and the resultant was stirred continuously at room temperature for 16 hours. After the reaction was halted by adding 3M hydrochloric acid to a reaction solution, an organic layer was separated and extracted from a water layer by using dichloromethane. The thus collected organic layer was washed by using 3M hydrochloric acid, water, a saturated sodium bicarbonate aqueous solution and brine in that order, and dried with anhydrous magnesium sulphate. Solvents were removed by distillation to obtain a slightly yellow solid. The thus obtained solid was purified by column chromatography (alumina, toluene) and also subjected to recrystallization (toluene/hexane), thereby obtaining a colourless scaly crystal of 51.5 g.

Workup

  1. temperaturemaintained
  2. customan organic layer was separated
  3. extractionextracted from a water layer
  4. washThe thus collected organic layer was washed
  5. dry with materiala saturated sodium bicarbonate aqueous solution and brine in that order, and dried with anhydrous magnesium sulphate
  6. customSolvents were removed by distillation
  7. customto obtain a slightly yellow solid
  8. customThe thus obtained solid was purified by column chromatography (alumina, toluene)
  9. customalso subjected to recrystallization (toluene/hexane)
  10. customobtaining a colourless scaly crystal of 51.5 g

Sources & evidence

ORD record
ord-ee560045976243e58fc3829849a20f95
Source dataset
uspto-grants-2010_02
Patent number
US07662442B2

Reaction notes

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