Hexamethylphosphoramide → HCID 57292408, compound

HRID 275433Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[CH2:12][CH:11]([CH3:15])[CH2:10][C:9]2=O)=[CH:4][CH:3]=1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:26]2)=CC=1.CN(C)P(N(C)C)(N(C)C)=O>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[CH2:12][CH:11]([CH3:15])[CH2:10][C:9]2=[S:26])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1.02 g (4.68 mmol) of N-(4'-fluorophenyl)-3-methylglutarimide (Compound 66), 0.88 g (2.2 mmol) of 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (known as Lawesson's Reagent), and 6 ml of hexamethylphosphoramide in a 50 ml round-bottomed flask was warmed to 95°-100° C. for 21 hours. An additional 1.05 g (2.5 mmol) of Lawesson's Reagent were added and heating to 100° C. was continued for an additional 30 hours. The mixture was allowed to cool to room temperature and water (50 ml) was added. The mixture was extracted with ether (4×50 ml). The organic portions were combined, dried over MgSO4 and the solvent was removed in vacuo. The resulting 2 g of orange oil were purified via flash chromatography (silica gel, 1:1 hexanes/methylene chloride) to yield 300 mg (28% yield) of yellow oil which solidified to a solid: m.p. 84.5°-87.5° C.

Workup

temperaturewas warmed to 95°-100° C. for 21 hours
temperatureto cool to room temperature
extractionThe mixture was extracted with ether (4×50 ml)
dry with materialdried over MgSO4
customthe solvent was removed in vacuo
customThe resulting 2 g of orange oil were purified via flash chromatography (silica gel, 1:1 hexanes/methylene chloride)

Sources & evidence

ORD record: ord-7164324f17e34336840e1a850a17e91d
Source dataset: uspto-grants-1995_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05393735

Reaction notes

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