Carbon Disulfide → HCID 10156540, compound

HRID 895329Notes

Reaction equation

HRID 895329 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]=[C:11]1[N:16]=[CH:15][C:14]([CH3:18])([CH3:17])[CH2:13][S:12]1)([CH3:3])[CH3:2].[C:19](=[S:21])=[S:20].[H-].[Na+].[CH2:24](Cl)[CH:25]=[CH2:26]>CN(C)C=O.O>[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]=[C:11]1[N:16]([C:19]([S:21][CH2:26][CH:25]=[CH2:24])=[S:20])[CH2:15][C:14]([CH3:18])([CH3:17])[CH2:13][S:12]1)([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 6348Carbon DisulfideHCID 7850Allyl chlorideHCID 24758Sodium hydrideHCID 223795002-(2-Isopropylphenyl)imino-5,5-dimethyl-1,3-thiazine

Product 1

HCID 10156540HCID 10156540, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(2-isopropylphenyl)imino-5,5-dimethyl-1,3-thiazine (0.26 g), carbondisulfide (0.10 g) in N,N-dimethylformamide (3 ml) was added 60% sodium hydride (0.05 g) under ice-cooling. The reaction mixture was stirred for 30 minutes. Allylchloride (0.10 g) was added thereto. The reaction mixture was stirred at 0° C. for 1 h. To a reaction mixture was added water (80 ml), extracted with diethylether (100 ml), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to give 2-(2-isopropylphenyl)imino-3-(allylthio)thiocarbonyl-5,5-dimethyl-1,3-thiazine (0.26 g, yield: 69%) as a pale yellow oil.

Workup

  1. temperaturecooling
  2. stirringThe reaction mixture was stirred at 0° C. for 1 h
  3. extractionextracted with diethylether (100 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-0e7b6afbbaf947f5815899b202fc17b4
Source dataset
uspto-grants-2005_07
Patent number
US06916806B2

Reaction notes

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