p-Toluenesulfonic acid → 1,3-Bis[(2-ethoxycarbonylethyl)thio]acetone ethoxycarbonylhydrazone

HRID 1108428Notes

Reaction equation

HRID 1108428 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][CH2:7][S:8][CH2:9][C:10]([CH2:12][S:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=O)=[O:5])[CH3:2].[C:21]([O:25][CH2:26][CH3:27])(=[O:24])[NH:22][NH2:23].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(#N)C>[CH2:26]([O:25][C:21]([NH:22][N:23]=[C:10]([CH2:12][S:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:9][S:8][CH2:7][CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])=[O:24])[CH3:27]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 158852831,3-Bis(2-ethoxycarbonylethylthio)acetone

Product 1

HCID 158852841,3-Bis[(2-ethoxycarbonylethyl)thio]acetone ethoxycarbonylhydrazoneYield 91.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1,3-bis[(2-ethoxycarbonylethyl)thio]acetone (6.22 g, 19.3 mmol), ethyl carbazate (2.40 g, 23.1 mmol) and a catalytic amount of p-toluenesulfonic acid in anhydrous acetonitrile (50 mL) containing molecular sieve was stirred for 2 days at room temperature. The reaction was quenched with water/ethyl acetate and filtered. The filtrate was extracted with ethyl acetate. The organic extract was washed with aqueous sodium bicarbonate, dried over sodium sulfate, and concentrated. The residue was triturated with hexane, affording 7.2 g of 1,3-bis[(2-ethoxycarbonylethyl)thio]acetone ethoxycarbonylhydrazone. 1H NMR (CDCl3) δ 2.2-2.4 (m, 9), 2.6-2.8 (m, 8H), 3.42 (s, 2H), 3.54 (s, 2H), 4.1-4.3 (m, 6H), 8.82 (br s, 1H).

Workup

  1. customThe reaction was quenched with water/ethyl acetate
  2. filtrationfiltered
  3. extractionThe filtrate was extracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with aqueous sodium bicarbonate
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was triturated with hexane

Sources & evidence

ORD record
ord-c54aa31cffec469fbbc7fb1d28ec0430
Source dataset
uspto-grants-2000_05
Patent number
US06066630

Reaction notes

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