1,2-Dichloroethane → HCID 86681582, compound

HRID 339434Notes

Reaction equation

HRID 339434 reaction equation
ClCCCl.C[Al](C)C.[CH2:9]([SH:11])[CH3:10].[CH:12]([O:15][N:16]=[C:17]([C:27]([O:29]C)=O)[C:18]([N:22]1[CH:26]=[N:25][CH:24]=[N:23]1)=[N:19][O:20][CH3:21])([CH3:14])[CH3:13]>C(OC(C)C)(C)C.O>[CH:12]([O:15][N:16]=[C:17]([C:18](=[N:19][O:20][CH3:21])[N:22]1[CH:26]=[N:25][CH:24]=[N:23]1)[C:27](=[O:29])[S:11][CH2:9][CH3:10])([CH3:13])[CH3:14]

Participants

7

Reactant 4

HCID 111,2-Dichloroethane2×HCID 6343EthanethiolHCID 16682925TrimethylaluminumHCID 86681583HCID 86681583, compound

Product 1

HCID 86681582HCID 86681582, compoundYield 98.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7914Diisopropyl EtherSolvent

Procedure

To 8 ml of 1,2-dichloroethane was added 7.5 ml (7.5 mmol) of a trimethylaluminum (1 mol/l) hexane solution. Thereinto was drop-wise added 0.47 g (7.5 mmol) of ethanethiol at room temperature, followed by stirring for 30 minutes. To this mixed solution was added, at room temperature, a 1,2-dichloroethane solution containing 0.50 g (1.9 mmol) of the 1-(2-isopropoxyimino-2-methoxycarbonyl-1-methoxyiminoethyl)-1H-1,2,4-triazole produced in Example 12, followed by stirring for 1.5 hours. The reaction mixture was diluted with isopropyl ether. Thereto was added a small amount of water, followed by stirring. The resulting precipitate was removed by filtration. The solvent was distilled off. The resulting residue was purified by silica gel column chromatography (elutant:ethyl acetate/hexane=1/2) to obtain 0.56 g (yield: 98%) of a title compound as a yellow oily matter.

Workup

  1. additionTo this mixed solution was added, at room temperature
  2. stirringby stirring for 1.5 hours
  3. stirringby stirring
  4. customThe resulting precipitate was removed by filtration
  5. distillationThe solvent was distilled off
  6. customThe resulting residue was purified by silica gel column chromatography (elutant:ethyl acetate/hexane=1/2)

Sources & evidence

ORD record
ord-c5c806aef2834e51b1986928e17f1166
Source dataset
uspto-grants-2014_11
Patent number
US08895035B2

Reaction notes

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