Dimethylformamide → 1-(3-Cyano-4-oxo-4H-1-benzopyran-6-yl)ethyl acetate

HRID 2083227Notes

Reaction equation

HRID 2083227 reaction equation
Br[CH:2]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH:11]=[C:10]([C:13]#[N:14])[C:9](=[O:15])[C:8]=2[CH:16]=1)[CH3:3].[C:17]([O-:20])(=[O:19])[CH3:18].[Na+].CN(C)C=O>O>[C:17]([O:20][CH:2]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH:11]=[C:10]([C:13]#[N:14])[C:9](=[O:15])[C:8]=2[CH:16]=1)[CH3:3])(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 517045Sodium AcetateHCID 203582246-(1-Bromoethyl)-4-oxo-4H-1-benzopyran-3-carbonitrile

Product 1

HCID 203582201-(3-Cyano-4-oxo-4H-1-benzopyran-6-yl)ethyl acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 5.56 parts of 6-(1-bromoethyl)-4-oxo-4H-1-benzopyran-3-carbonitrile, 1.640 parts of anhydrous sodium acetate and 8 parts by volume of dimethylformamide is heated at 70° C under stirring for 50 minutes. After cooling, the reaction mixture is poured into 100 parts by volume of water to give precipitates, which are collected and recrystallized from ethanol and subsequently ethyl acetate. The procedure yields 2.90 parts of 6-(1-acetoxy-ethyl)-4-oxo-4H-1-benzopyran-3-carbonitrile. Melting point: 148°-149° C

Workup

  1. temperatureAfter cooling
  2. customto give
  3. customprecipitates
  4. customwhich are collected
  5. customrecrystallized from ethanol and subsequently ethyl acetate

Sources & evidence

ORD record
ord-1f04cdfe96ca4084b6c7976e3ff36443
Source dataset
uspto-grants-1978_04
Patent number
US04085116

Reaction notes

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