Triethylamine → HCID 65640837, compound

HRID 1498939Notes

Reaction equation

HRID 1498939 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=[N:12]OS(C1C=CC(C)=CC=1)(=O)=O)[C:10]#[N:11].C(N(CC)CC)C.[C:31]([O:35][CH2:36][CH3:37])(=[O:34])[CH2:32][SH:33]>C(O)C>[NH2:11][C:10]1[C:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])=[N:12][S:33][C:32]=1[C:31]([O:35][CH2:36][CH3:37])=[O:34]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12185Ethyl ThioglycolateHCID 86679350HCID 86679350, compound

Product 1

HCID 65640837HCID 65640837, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol (100 ml), (2,4-dichlorophenyl)-O-(p-toluenesulfonyl)hydroxyiminoacetonitrile (10.0 g, 27.1 mmol) prepared in the Step 27-1-2 was dissolved, and triethylamine (3.0 g) and ethyl thioglycolate (4.72 g) were added thereto. The mixture was stirred for one hour at a room temperature. The solvent was distilled off. The residue was dissolved in diethyl ether, washed with water, and dried over anhydrous magnesium sulfate. The resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:3) to give the title compound (4.81 g, 56%).

Workup

  1. dissolutionwas dissolved
  2. distillationThe solvent was distilled off
  3. dissolutionThe residue was dissolved in diethyl ether
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:3)

Sources & evidence

ORD record
ord-b1e9b859c8bc4ab59c68a5cf4be07cf4
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

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