Dimethylcarbamoyl Chloride → HCID 21444460, compound

HRID 328232Notes

Reaction equation

HRID 328232 reaction equation
[H-].[Na+].O1CCCC1.[CH3:8][C:9]1[CH:10]=[C:11]([OH:23])[CH:12]=[C:13]([CH3:22])[C:14]=1[S:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1.[CH3:24][N:25]([CH3:29])[C:26](Cl)=[O:27]>O>[CH3:24][N:25]([CH3:29])[C:26](=[O:27])[O:23][C:11]1[CH:12]=[C:13]([CH3:22])[C:14]([S:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[C:9]([CH3:8])[CH:10]=1

Participants

6

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 8028Tetrahydrofuran3×HCID 24758Sodium hydrideHCID 214444563,5-Dimethyl-4-[(pyridin-2-yl)sulfanyl]phenol

Product 1

HCID 21444460HCID 21444460, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred suspension of 240 mg. of sodium hydride in 20 ml. of dry tetrahydrofuran is added a solution of 2.31 g. of 3,5-dimethyl-4-(2-pyridylthio)phenol in 30 ml. of dry tetrahydrofuran. After the effervescence has subsided, a solution of 1.1 g. of N,N-dimethylcarbamoyl chloride in 10 ml. of dry tetrahydrofuran is added dropwise. The reaction mixture is stirred at ambient temperature for 16 hours, and then under reflux for 4 hours. The reaction mixture is cooled to room temperature, and then diluted with an excess of water. The product is extracted into ethyl acetate. The ethyl acetate is washed with water, dried using anhydrous magnesium sulfate, and then evaporated in vacuo to give crude 3,5-dimethyl-4-(2-pyridylthio)phenyl N,N-dimethylcarbamate. The crude product can be purified further by recrystallization.

Workup

  1. additionTo a stirred suspension of 240 mg
  2. temperatureunder reflux for 4 hours
  3. temperatureThe reaction mixture is cooled to room temperature
  4. extractionThe product is extracted into ethyl acetate
  5. washThe ethyl acetate is washed with water
  6. customdried
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-39913770e708484b8c8abff61f6646fd
Source dataset
uspto-grants-1977_04
Patent number
US04016278

Reaction notes

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