Dichloromethane → 2-(2-methoxyphenethyl)imino-N-(ethylthiocarbamoyl)-5,5-dimethyl-1,3-thiazine

HRID 2415061Notes

Reaction equation

HRID 2415061 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][CH:17]=[CH:16][C:4]=1[CH2:5][CH2:6][N:7]=[C:8]1[N:13]=[CH:12][C:11]([CH3:15])([CH3:14])[CH2:10][S:9]1.[CH2:20]([N:22]([CH2:25]C)CC)[CH3:21].ClCCl.C(Cl)(=[S:34])OCC>O>[CH3:1][O:2][C:3]1[CH:19]=[CH:18][CH:17]=[CH:16][C:4]=1[CH2:5][CH2:6][N:7]=[C:8]1[N:13]([C:25](=[S:34])[NH:22][CH2:20][CH3:21])[CH2:12][C:11]([CH3:15])([CH3:14])[CH2:10][S:9]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 5325481O-ethyl chloromethanethioateHCID 226399872-(2-Methoxyphenethyl)imino-5,5-dimethyl-1,3-thiazine

Product 1

HCID 226399822-(2-methoxyphenethyl)imino-N-(ethylthiocarbamoyl)-5,5-dimethyl-1,3-thiazineYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-(2-methoxyphenethyl)imino-5,5-dimethyl-1,3-thiazine (0.28 g), triethylamine (0.15 g) and dichloromethane (5 ml) was added dropwise for 3 minutes ethyl chlorothiocarbonate (0.15 g). The mixture was stirred at room temperature for 2 hours. 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 2-(2-methoxyphenethyl)imino-N-(ethylthiocarbamoyl)-5,5-dimethyl-1,3-thiazine (0.21 g, yield: 60%) 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-3ea8d6f3882347bb87c2fb1a22691ec1
Source dataset
uspto-grants-2004_11
Patent number
US06818640B1

Reaction notes

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