Dichloromethane → 3-(Ethylthiocarbonyl)-2-(2-isopropylphenyl)imino-5,5-dimethyl-1,3-thiazine

HRID 350631Notes

Reaction equation

HRID 350631 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].[CH2:19](N(CC)CC)[CH3:20].ClCCl.[C:29](Cl)(=[S:33])OCC>O>[CH2:19]([C:29]([N:16]1[CH2:15][C:14]([CH3:18])([CH3:17])[CH2:13][S:12][C:11]1=[N:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH:1]([CH3:3])[CH3:2])=[S:33])[CH3:20]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 5325481O-ethyl chloromethanethioateHCID 223795002-(2-Isopropylphenyl)imino-5,5-dimethyl-1,3-thiazine

Product 1

HCID 865984883-(Ethylthiocarbonyl)-2-(2-isopropylphenyl)imino-5,5-dimethyl-1,3-thiazineYield 57.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-(2-isopropylphenyl)imino-5,5-dimethyl-1,3-thiazine (1.00 g), triethylamine (0.58 g) and dichloromethane (5 ml) was added dropwise for 5 minutes ethyl chlorothiocarbonate (0.56 g). The mixture was stirred at room temperature for 1 hour. To the solution was added water (30 ml). The mixture was extracted with diethylether (60 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 3-(ethylthiocarbonyl)-2-(2-isopropylphenyl)imino-5,5-dimethyl-1,3-thiazine (0.74 g, yield: 56%) as colorless oil.

Workup

  1. extractionThe mixture was extracted with diethylether (60 ml)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-8dc91f0bc7b64a71be2d8dd1356632ee
Source dataset
uspto-grants-2007_02
Patent number
US07183275B2

Reaction notes

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