Water → HCID 16662172, compound

HRID 548636Notes

Reaction equation

HRID 548636 reaction equation
[N:1]1([CH2:8][C@H:9]2[N:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][N:24]4[CH2:28][CH2:27][CH2:26][CH:25]4[CH3:29])=[CH:16][CH:15]=3)[C:12](=O)[CH2:11][CH2:10]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:40]2)=CC=1.C1(C)C=CC=CC=1.O>C(Cl)(Cl)Cl>[N:1]1([CH2:8][C@H:9]2[N:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][N:24]4[CH2:28][CH2:27][CH2:26][CH:25]4[CH3:29])=[CH:16][CH:15]=3)[C:12](=[S:40])[CH2:11][CH2:10]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 87949Lawesson's reagent2×HCID 16662171HCID 16662171, compound

Product 1

HCID 16662172HCID 16662172, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

(5S)-5-(azepan-1-ylmethyl)-1-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}pyrrolidin-2-one 20 (0.1 g, 0.24 mmol, 1 eq) is dissolved in chloroform (5 ml) and 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide a49 (Lawesson's reagent, 0.05 g, 0.12 mmol, 0.5 eq) is added. Toluene (5 ml) is added and the mixture is refluxed for 6 h. Water is then added, and after phase separation, the organic layer is dried over magnesium sulfate and concentrated to give 0.2 g of crude material. Purification by chromatography over silicagel (dichloromethane/methanol/ammonia 94/6/0.6) affords 0.05 g of pure (5S)-5-(azepan-1-ylmethyl)-1-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}pyrrolidine-2-thione 21.

Workup

  1. temperaturethe mixture is refluxed for 6 h
  2. customafter phase separation
  3. dry with materialthe organic layer is dried over magnesium sulfate
  4. concentrationconcentrated
  5. customto give 0.2 g of crude material
  6. customPurification by chromatography over silicagel (dichloromethane/methanol/ammonia 94/6/0.6)

Sources & evidence

ORD record
ord-8c1a1f6a32a749bb89dce308a2a74f1e
Source dataset
uspto-grants-2011_05
Patent number
US07943605B2

Reaction notes

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