Dabco → HCID 86625223, compound

HRID 1640385Notes

Reaction equation

HRID 1640385 reaction equation
N12CCN(CC1)CC2.[CH3:9][N:10]([CH3:14])[C:11](Cl)=[S:12].[Cl:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]([CH3:26])[C:17]=1[OH:27]>CN(C)C=O>[Cl:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]([CH3:26])[C:17]=1[O:27][C:11]([N:10]([CH3:14])[CH3:9])=[S:12]

Participants

5

Reactant 3

HCID 9237DabcoHCID 27871Dimethylthiocarbamoyl chlorideHCID 22559906HCID 22559906, compound

Product 1

HCID 86625223HCID 86625223, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under an atmosphere of nitrogen, 12.3 g (109.7 mmol) of 1,4-diazabicyclo[2.2.2]octane and then 13.6 g (109.7 mmol) of dimethylaminothiocarbonyl chloride were added to 11.0 g (54.8 mmol) of methyl 4-chloro-3-hydroxy-2-methylbenzoate in 200 ml of N,N-dimethylformamide. The mixture was stirred at room temperature (RT) for 16 h and, for work-up, poured on ice-water. The product precipitated out and was removed by filtration. The residue was washed with 1M HCl. This gave 14.7 g of clean product.

Workup

  1. additionfor work-up, poured on ice-water
  2. customThe product precipitated out
  3. customwas removed by filtration
  4. washThe residue was washed with 1M HCl

Sources & evidence

ORD record
ord-149e1a89b99444019e3f3388dbd3a51d
Source dataset
uspto-grants-2012_02
Patent number
US08114816B2

Reaction notes

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