Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dabco | HCID 9237 | — |
| Reactant | Dimethylthiocarbamoyl chloride | HCID 27871 | — |
| Reactant | Benzoic acid, 2-hydroxy-4-methyl-, methyl ester | HCID 78400 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 19866619 | HCID 19866619 | 82.3% |
Reaction Steps
To a solution of methyl 2-hydroxy-4-methylbenzoate (109 g, 657.2 mmol) and 1,4-diazabicyclo[2.2.2]octane (147.4 g, 1314.4 mmol) in N,N-dimethylformamide (300 mL) was added a solution of N,N-dimethylcarbamothioyl chloride (97.5 g, 788.6 mmol) in N,N-dimethylformamide (100 mL) at room temperature. After being heated at 60° C. for 4 hours, the mixture was cooled and poured onto ice. The formed precipitate was collected by filtration, washed with water (300 mL×3) and dried in vacuo to afford 137 g of methyl 2-[(dimethylcarbamothioyl)oxy]-4-methylbenzoate as an off-white solid (yield was 82%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08871756B2 |
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| Source dataset | uspto-grants-2014_10 |
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| ORD ID | ord-b1dacbc56b944ee29df2a43315996909 |
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| Source note | uspto-grants-2014_10 |
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