Dabco → HCID 19866619, compound

HRID 539950Notes

Reaction equation

HRID 539950 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].N12CCN(CC1)CC2.[CH3:21][N:22]([CH3:26])[C:23](Cl)=[S:24]>CN(C)C=O>[CH3:21][N:22]([CH3:26])[C:23]([O:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])=[S:24]

Participants

5

Reactant 3

HCID 9237DabcoHCID 27871Dimethylthiocarbamoyl chlorideHCID 78400Benzoic acid, 2-hydroxy-4-methyl-, methyl ester

Product 1

HCID 19866619HCID 19866619, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

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%).

Workup

  1. temperaturethe mixture was cooled
  2. additionpoured onto ice
  3. filtrationThe formed precipitate was collected by filtration
  4. washwashed with water (300 mL×3)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-b1dacbc56b944ee29df2a43315996909
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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