O-Xylene → HCID 18412295, compound

HRID 2288337Notes

Reaction equation

F[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[NH:11][C:12](=O)[CH2:13][O:14][CH3:15].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:26])=CC=1.[C:39]1([CH3:46])C(C)=CC=CC=1>C1(C)C=CC=CC=1>[CH2:39]([O:8][C:6]([C:5]1[CH:9]=[CH:10][C:2]2[S:26][C:12]([CH2:13][O:14][CH3:15])=[N:11][C:3]=2[CH:4]=1)=[O:7])[CH3:46]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 3.0 g (11.7 mMol) of 4-fluoro-3-methoxyacetamido-benzoic acid and 2.1 g (5.2 mMol) of Lawesson's reagent was refluxed for 6 hours in 90 ml toluene, mixed with 1.0 g Lawesson's reagent and heated to 120° C. for another 6 hours. After the solvent was replaced with xylene the mixture was heated to 180° C. for a further 8 hours in a pressurised vessel. Then the solvent was distilled off in vacuo, the crude product obtained was purified by flash chromatography (silica gel; ethyl acetate/petroleum ether=5:95) and evaporated down again. Yield: 2.1 g of yellow crystals (72% of theory), Rf value: 0.55 (silica gel; ethyl acetate/petroleum ether=3:7)

Workup

temperaturewas heated to 180° C. for a further 8 hours in a pressurised vessel
distillationThen the solvent was distilled off in vacuo

Sources & evidence

ORD record: ord-9f63e10e078e4014a533d86ba5d63382
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06087380

Reaction notes

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