Lawesson's reagent → HCID 58155199, compound

HRID 1929474Notes

Reaction equation

[C:1](=[N:14][C:15]1[CH:16]=[CH:17][C:18]([F:31])=[C:19]([C:21]2([CH:28]3[CH2:30][CH2:29]3)[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:41])=CC=1>O1CCCC1.C(OCC)(=O)C>[C:1](=[N:14][C:15]1[CH:16]=[CH:17][C:18]([F:31])=[C:19]([C:21]2([CH:28]3[CH2:30][CH2:29]3)[NH:26][C:25](=[S:41])[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: 70 °C

Procedure

A mixture of (RS)-5-[5-(benzhydrylidene-amino)-2-fluoro-phenyl]-5-cyclopropyl-morpholin-3-one (2.10 g, 5.07 mmol) and Lawesson's reagent (0.926 mg, 2.3 mmol) in tetrahydrofuran (15 mL) was stirred at 70° C. for 3 hours. For the workup, the reaction mixture was diluted with ethyl acetate and extracted with a saturated solution of sodium hydrogen-carbonate. The organic layer was dried over sodium sulfate and evaporated. The crude product was purified by chromatography on silica gel using a gradient of hexane/ethyl acetate as the eluent. The (RS)-5-[5-(benzhydrylidene-amino)-2-fluoro-phenyl]-5-cyclopropyl-morpholine-3-thione was obtained as a yellow foam (1.42 g, 65% of theory). Mass (calculated) C26H23FN2OS [430.545]; (found) [M+H]+=431.

Workup

extractionextracted with a saturated solution of sodium hydrogen-carbonate
dry with materialThe organic layer was dried over sodium sulfate
customevaporated
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-e7e546a9fbfd43a5b0c43bad310c1296
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188079B2

Reaction notes

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