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

HRID 2415054Notes

Reaction equation

HRID 2415054 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(N(CC)CC)C.ClCCl.[C:29](Cl)(=[O:33])[O:30][CH2:31][CH3:32]>O>[CH2:31]([O:30][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])=[O:33])[CH3:32]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 223795002-(2-Isopropylphenyl)imino-5,5-dimethyl-1,3-thiazine

Product 1

HCID 121467813-(Ethoxycarbonyl)-2-(2-isopropylphenyl)imino-5,5-dimethyl-1,3-thiazineYield 68.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-(2-isopropylphenyl)imino-5,5-dimethyl-1,3-thiazine (0.26 g), triethylamine (0.15 g) and dichloromethane (5 ml) was added dropwise for 5 minutes ethyl chlorocarbonate (0.13 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 3-(ethoxycarbonyl)-2-(2-isopropylphenyl)imino-5,5-dimethyl-1,3-thiazine (0.23 g, yield: 68%) as a white crystal. M.p. 84-86° C.

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-ae524c99f09f49ecb13e48b1c496146d
Source dataset
uspto-grants-2004_11
Patent number
US06818640B1

Reaction notes

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