Dimethylformamide → Methyl 2-[(dimethylcarbamothioyl)-oxy]-4-methoxybenzoate

HRID 1249460Notes

Reaction equation

[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].N12CCN(CC1)CC2.CN(C)C=O.[CH3:27][N:28]([CH3:32])[C:29](Cl)=[S:30]>O>[CH3:27][N:28]([C:29](=[S:30])[O:1][C:2]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])[CH3:32]

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of 350 g of methyl 2-hydroxy-4-methoxybenzoate, 648 g of 1,4-diazabicyclo[2.2.2]-octane (DABCO) and 3 L of dimethylformamide was added 712 g of dimethylthiocarbamoyl chloride. The mixture was warmed to 50° C. and held for 7 hours, then allowed to cool overnight. The mixture was poured into 10 L water; the aqueous mixture was extracted with 8 L of benzene-hexane (4:1). The organic solution was washed with 1N HCl, 10% NaOH, and dried over magnesium sulfate. Evaporation of the solvent in vacuo gave 396 g of the title compound, m.p. 95°-105° C. Further extraction of the aqueous mixture gave additional product, 171 g, m.p. 117°-120° C. Recrystallization of a portion of the crude product from methanol gave pure material, m.p. 122°-124° C.

Workup

temperatureto cool overnight
extractionthe aqueous mixture was extracted with 8 L of benzene-hexane (4:1)
washThe organic solution was washed with 1N HCl, 10% NaOH
dry with materialdried over magnesium sulfate
customEvaporation of the solvent in vacuo

Sources & evidence

ORD record: ord-1baab6f9899a46e39fe5a42601d3522f
Source dataset: uspto-grants-1986_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04632693

Reaction notes

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