Ethyl Acetate → HCID 44614678, compound

HRID 1911234Notes

Reaction equation

HRID 1911234 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([N+:11]([O-])=O)=[CH:4][N:3]=1.[C:14]([O:20][CH2:21][C:22](N)=[S:23])(=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16].C(OCC)(=O)C>S1(CCCC1)(=O)=O>[CH3:16][C:15]([CH3:18])([CH3:17])[C:14]([O:20][CH2:21][C:22]1[S:23][C:4]2[C:5]([N:11]=1)=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[CH:2][N:3]=2)=[O:19]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 757382-Chloro-3,5-dinitropyridineHCID 27821132-Amino-2-thioxoethyl 2,2-dimethylpropanoate

Product 1

HCID 44614678HCID 44614678, compoundYield 16.7%

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 6 g (29.48 mmol) of 2-chloro-3,5-dinitropyridine and 7.74 g (44.22 mmol) of 2-amino-2-thioxoethyl pivalate in 50 mL of sulfolane is heated for 2 hours at 105° C. After this time, 150 mL of ethyl acetate are added to the mixture, and the organic phase is washed three times with 200 mL of water and then once with 100 mL of saturated sodium chloride solution. The organic phase is then separated out, dried over sodium sulfate and then concentrated under reduced pressure. The product obtained is purified by chromatography on a column of silica, eluting with a mixture of heptane and ethyl acetate. 1.45 g of a yellow solid are obtained.

Workup

  1. washthe organic phase is washed three times with 200 mL of water
  2. customThe organic phase is then separated out
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe product obtained
  6. customis purified by chromatography on a column of silica
  7. washeluting with a mixture of heptane and ethyl acetate

Sources & evidence

ORD record
ord-64d1a209e8344fb9bde98addbb16824e
Source dataset
uspto-grants-2013_12
Patent number
US08604050B2

Reaction notes

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