Lawesson's reagent → (R)-5-[5-(Benzhydrylidene-amino)-2-fluoro-phenyl]-5-methyl-morpholine-3-thione

HRID 593368Notes

Reaction equation

[C:1](=[N:14][C:15]1[CH:16]=[CH:17][C:18]([F:29])=[C:19]([C@@:21]2([CH3:28])[NH:26][C:25](=O)[CH2:24][O:23][CH2:22]2)[CH:20]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:39])=CC=1>O1CCOCC1>[C:1](=[N:14][C:15]1[CH:16]=[CH:17][C:18]([F:29])=[C:19]([C@@:21]2([CH3:28])[NH:26][C:25](=[S:39])[CH2:24][O:23][CH2:22]2)[CH:20]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of (R)-5-[5-(benzhydrylidene-amino)-2-fluoro-phenyl]-5-methyl-morpholin-3-one (1.53 g, 3.94 mmol) in dioxane (30 ml) was treated with Lawesson's reagent (1.3 g, 3.15 mmol). The orange coloured suspension was heated in a sealed tube at 80° C. for 18 hours. For the workup, the meanwhile green coloured reaction mixture was evaporated at reduced pressure and the residue directly purified by flash chromatography on a silica-amine phase using a gradient of heptane/ethyl acetate=100:0 to 40:60 as the eluent. The (R)-5-[5-(benzhydrylidene-amino)-2-fluoro-phenyl]-5-methyl-morpholin-3-thione was obtained as a yellow solid (0.803 g, 50%); (calculated) C24H21FN2OS [404.51]; (found) [M+H]+=405.

Workup

customFor the workup, the meanwhile green coloured reaction mixture
customwas evaporated at reduced pressure
customthe residue directly purified by flash chromatography on a silica-amine phase

Sources & evidence

ORD record: ord-adaa4a0414364074b4d79ea12590aae4
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242943B2

Reaction notes

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