Ethyl Acetate → HCID 44614678, compound

HRID 2069523Notes

Reaction equation

HRID 2069523 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-0e98b376f5fe4128b3eb5aa0e1d6721d
Source dataset
uspto-grants-2012_10
Patent number
US08299114B2

Reaction notes

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