Lawesson's reagent → HCID 86668500, compound

HRID 1946923Notes

Reaction equation

HRID 1946923 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([C:15]3[CH:16]=[N:17][C:18]([O:21][CH:22]([F:24])[F:23])=[CH:19][CH:20]=3)[NH:13][C:12](=O)[CH2:11][O:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:34])=CC=1>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([C:15]3[CH:16]=[N:17][C:18]([O:21][CH:22]([F:24])[F:23])=[CH:19][CH:20]=3)[NH:13][C:12](=[S:34])[CH2:11][O:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 68153562HCID 68153562, compound

Product 1

HCID 86668500HCID 86668500, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (RS)-5-(3-bromo-phenyl)-5-(6-difluoromethoxy-pyridin-3-yl)-morpholin-3-one (1.6 g, 1.0 eq) and Lawesson's reagent (2.0 g, 1.2 eq) in tetrahydrofuran (60 ml) was stirred at room temperature overnight. For the workup, the solvent was removed at reduce pressure. The crude product was purified by chromatography on silica gel using a gradient of hexane/ethyl acetate as the eluent. The (RS)-5-(3-bromo-phenyl)-5-(6-difluoromethoxy-pyridin-3-yl)-morpholin-3-thione was obtained as a yellow foam (1.0 g, 83% of theory). MS (ISP): m/z=415 [M+H]+.

Workup

  1. customFor the workup, the solvent was removed
  2. customThe crude product was purified by chromatography on silica gel using a gradient of hexane/ethyl acetate as the eluent

Sources & evidence

ORD record
ord-7f3eaedaadfd424dac9fba624c426e97
Source dataset
uspto-grants-2013_03
Patent number
US08399459B2

Reaction notes

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