Ethyl Acetate → HCID 23047252, compound

HRID 2107044Notes

Reaction equation

HRID 2107044 reaction equation
[CH3:1][CH:2]1[S:7][C:6](=[O:8])[NH:5][N:4]=[C:3]1[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=[O:18])[C:12]2([CH3:20])[CH3:19].[H-].[Na+].Cl[C:24]([O:26][CH2:27][CH3:28])=[O:25].C(OCC)(=O)C>CN(C=O)C>[CH3:1][CH:2]1[S:7][C:6](=[O:8])[NH:5][N:4]=[C:3]1[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:13](=[O:18])[C:12]2([CH3:19])[CH3:20]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10928Ethyl chloroformateHCID 24758Sodium hydrideHCID 15111517HCID 15111517, compound

Product 1

HCID 23047252HCID 23047252, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
20 °C

Procedure

1.16 g 5-(3,6-Dihydro-6-methyl-2-oxo-2H-1,3,4-thiadiazin-5-yl)-1,3-dihydro-3,3-dimethyl-2H-indol-2-one (Example 3) in 30 ml DMF were cooled to 0° C. 0.175 g sodium hydride from a 55% dispersion in mineral oil was added and the mixture was successively stirred for 0.5 hr at 0° C. and 0.5 hr at 20° C. After cooling to 0° C. a solution of 0.43 g ethyl chloroformate in 2 ml DMF was added dropwise. The reactional mixture was stirred at room temperature for 16 hrs, 250 ml ethyl acetate were added and the organic solution was washed with water. The aqueous phase was extracted with 2×100 ml methylene chloride and the organic solutions were mixed, dried on magnesium sulfate and evaporated to dryness. The residue was purified by chromatography on silica (methylene chloride-ethyl acetate: 4/1) then washed with isopropyl ether to yield 1.11 g of crystals.

Workup

  1. additionwas added dropwise
  2. stirringThe reactional mixture was stirred at room temperature for 16 hrs
  3. washthe organic solution was washed with water
  4. extractionThe aqueous phase was extracted with 2×100 ml methylene chloride
  5. additionthe organic solutions were mixed
  6. customdried on magnesium sulfate
  7. customevaporated to dryness
  8. customThe residue was purified by chromatography on silica (methylene chloride-ethyl acetate: 4/1)
  9. washthen washed with isopropyl ether

Sources & evidence

ORD record
ord-d49aaeedce5e489aa35ebabd7b6ab730
Source dataset
uspto-grants-1990_06
Patent number
US04933336

Reaction notes

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