Phosphorus oxide (P4O10) → 3,3-dimethyl-6-methylthio-2,4(1H,3H)-quinolinedione

HRID 2268778Notes

Reaction equation

O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[CH3:15][S:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:31])[C:25]([CH3:30])([CH3:29])[C:26]([OH:28])=O)=[CH:19][CH:18]=1>CS(O)(=O)=O>[CH3:29][C:25]1([CH3:30])[C:26](=[O:28])[C:19]2[C:20](=[CH:21][CH:22]=[C:17]([S:16][CH3:15])[CH:18]=2)[NH:23][C:24]1=[O:31]

Participants

Conditions

Temperature: 70 °C

Procedure

Phosphorus pentoxide (4.49 g, 0.032 mol) was added to a stirred solution of N-(4-methylthiophenyl)-2,2-dimethylmalonamic acid (5.0 g, 0.020 mol) in methanesulfonic acid (35 ml). The reaction mixture was warmed to 70° C. and stirred for 90 mins. The product mixture was then cooled to room temperature and poured over ice. The product was extracted with ethyl acetate (2×200 ml). The organic extracts were combined, washed with water (200 ml), saturated sodium hydrogen carbonate solution (200 ml), dried (MgSO4) and concentrated in vacuo to give 3,3-dimethyl-6-methylthio-2,4(1H,3H)-quinolinedione as a yellow solid. Mp 152° C.

Workup

temperatureThe product mixture was then cooled to room temperature
additionpoured over ice
extractionThe product was extracted with ethyl acetate (2×200 ml)
washwashed with water (200 ml), saturated sodium hydrogen carbonate solution (200 ml)
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-1442e6c8a85a4d12a13c0f24304c7fa4
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06329366B1

Reaction notes

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