Water → 4-azido-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran

HRID 344771Notes

Reaction equation

HRID 344771 reaction equation
Cl[CH:2]1[C:7]2[CH:8]=[C:9]([C:12]#[N:13])[CH:10]=[CH:11][C:6]=2[O:5][C:4]([CH3:15])([CH3:14])[CH2:3]1.[N-:16]=[N+:17]=[N-:18].[Na+].O>CN(C)C=O>[N:16]([CH:2]1[C:7]2[CH:8]=[C:9]([C:12]#[N:13])[CH:10]=[CH:11][C:6]=2[O:5][C:4]([CH3:15])([CH3:14])[CH2:3]1)=[N+:17]=[N-:18]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 537676584-Chloro-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran

Product 1

HCID 101051694-azido-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-chloro-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran(3g) and sodium azide (0.9g) in N,N-dimethylformamide (20 ml) was stirred for 3 days at room temperature. Water was added and the mixture extracted with ethyl acetate, the organic phase was separated and further washed with water, then dried over anhydrous sodium sulphate. Filtration and evaporation of the solvent in vacuo gave the title compound (3.03g) as a solid, which was used in the next step without further purification.

Workup

  1. extractionthe mixture extracted with ethyl acetate
  2. customthe organic phase was separated
  3. washfurther washed with water
  4. dry with materialdried over anhydrous sodium sulphate
  5. filtrationFiltration and evaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-ff09516856ad47beb0c09010e4f766a7
Source dataset
uspto-grants-1991_10
Patent number
US05053427

Reaction notes

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