Hydrochloric Acid → HCID 131729038, compound

HRID 1014087Notes

Reaction equation

HRID 1014087 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9][CH2:10][C@@H:11]([CH3:14])[CH2:12][OH:13].[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.C(N(CC)CC)C.Cl>CN(C)C1C=CN=CC=1.C(Cl)Cl.C(OC(C)C)(C)C.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9][CH2:10][C@@H:11]([CH3:14])[CH2:12][OH:13].[CH3:25][C:15]1[CH:20]=[CH:19][C:18]([S:21]([O-:2])(=[O:23])=[O:22])=[CH:17][CH:16]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 21055336HCID 21055336, compound

Product 1

HCID 131729038HCID 131729038, compound

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 7914Diisopropyl EtherSolvent

Procedure

10 ml of methylene chloride, 2 g (9.4 mmol) of (S)-3-(2-methoxyphenylsulfanyl)-2-methylpropanol, 2 g (10.5 mmol) of para-toluenesulfonyl chloride and 115 mg (0.94 mmol) of 4-dimethylaminopyridine are introduced into a three-necked flask under an inert atmosphere and 1.2 g (12.1 mmol) of triethylamine are then added dropwise. After stirring for 2 hours at ambient temperature, 10 ml of demineralised water are added. The pH is adjusted to 6.5 by adding 2N hydrochloric acid. The phases are separated and then the organic phase is washed with 10 ml of demineralised water. The organic phase is concentrated under reduced pressure. The yellow oil obtained (3.2 g) is taken up in a mixture of methylene chloride (4.8 ml) and 19.2 ml of isopropyl ether. The precipitate obtained is filtered off and then washed twice with 10 ml of isopropyl ether and dried at 40° C. under reduced pressure. The title product (3) is obtained in the form of a white powder 2.6 g (75%).

Workup

  1. additionare then added dropwise
  2. customThe phases are separated
  3. washthe organic phase is washed with 10 ml of demineralised water
  4. concentrationThe organic phase is concentrated under reduced pressure
  5. customThe yellow oil obtained (3.2 g)
  6. customThe precipitate obtained
  7. filtrationis filtered off
  8. washwashed twice with 10 ml of isopropyl ether
  9. customdried at 40° C. under reduced pressure

Sources & evidence

ORD record
ord-c1958916911947d2b39bea9b2c9a571e
Source dataset
uspto-grants-2011_07
Patent number
US07982054B2

Reaction notes

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