Sodium hydride → HCID 14838224, compound

HRID 358826Notes

Reaction equation

HRID 358826 reaction equation
[H-].[Na+].[OH:3][C:4]1[C:13]([CH2:14][C:15]([CH3:17])=[CH2:16])=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7].[CH3:18][N:19]([CH3:23])[C:20](Cl)=[S:21]>CN(C)C=O>[CH3:18][N:19]([C:20](=[S:21])[O:3][C:4]1[C:13]([CH2:14][C:15]([CH3:17])=[CH2:16])=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])[CH3:23]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27871Dimethylthiocarbamoyl chlorideHCID 14739011Methyl 2-hydroxy-3-(2-methylprop-2-en-1-yl)benzoate

Product 1

HCID 14838224HCID 14838224, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To 1 liter of dry dimethylformamide were added 16 g of 60% sodium hydride in oil. After stirring under a nitrogen atmosphere, 81.7 g of 2-hydroxy-3-(2-methyl-2-propenyl) benzoic acid, methyl ester, as a solution in dimethylformamide, were added in dropwise fashion. After stirring at room temperature, a solution 49.6 g of dimethylthiocarbamoyl chloride in dimethylformamide was added over a one hour period. The reaction mixture was stirred at room temperature overnight, then poured onto ice and extracted with diethyl ether and ethyl acetate. The combined organic extracts were washed successively with a 10% sodium hydroxide solution and water, dried over sodium sulfate, and concentrated in vacuo. The residue was vacuum distilled, and the fraction distilling at 162°-168° C. and 0.6 torr provided 69.9 g of the desired subtitle intermediate. NMR, MS.

Workup

  1. stirringAfter stirring at room temperature
  2. stirringThe reaction mixture was stirred at room temperature overnight
  3. additionpoured onto ice
  4. extractionextracted with diethyl ether and ethyl acetate
  5. washThe combined organic extracts were washed successively with a 10% sodium hydroxide solution and water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. distillationdistilled
  9. distillationthe fraction distilling at 162°-168° C.

Sources & evidence

ORD record
ord-fb50c42f52e3431f9b4bb4e21c51d408
Source dataset
uspto-grants-1991_03
Patent number
US04997956

Reaction notes

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