Lawesson's reagent → HCID 86668498, compound

HRID 1946907Notes

Reaction equation

HRID 1946907 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]2([CH3:16])[NH:14][C:13](=O)[CH2:12][O:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8].COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:26]2)=CC=1>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:9]2([CH3:16])[NH:14][C:13](=[S:26])[CH2:12][O:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 68153346HCID 68153346, compound

Product 1

HCID 86668498HCID 86668498, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A solution of the (RS)-5-(3-bromo-4-fluoro-phenyl)-5-methyl-morpholin-3-one (intermediate X-4) (265 mg, 0.9 mmol) in tetrahydrofuran (5.3 ml) was treated with 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide (Lawesson's reagent) (380 mg, 0.9 mmol). After 2.5 hours stirring at 70° C. the reaction mixture was evaporated at reduced pressure. The crude product was purified by chromatography on silica gel using a gradient of heptane/ethyl acetate=100/0 to 0/100 as the eluent. The (RS)-5-(3-bromo-4-fluoro-phenyl)-5-methyl-morpholin-3-thione was obtained as a light yellow gum (262 mg, 94% of theory). MS (ISP): m/z=302.2 [M−H]−, 304.1 [M+2−H]−.

Workup

  1. customwas evaporated at reduced pressure
  2. customThe crude product was purified by chromatography on silica gel using a gradient of heptane/ethyl acetate=100/0 to 0/100 as the eluent

Sources & evidence

ORD record
ord-04b5a04dc59649aebc96e6084414d418
Source dataset
uspto-grants-2013_03
Patent number
US08399459B2

Reaction notes

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