Sodium Hydroxide → HCID 178441992, compound

HRID 2351872Notes

Reaction equation

HRID 2351872 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[O:5][CH:6]([CH3:11])[CH2:7][CH2:8][C:9]#[N:10].[N-:15]=[N+:16]=[N-:17].[Na+].[Cl-].[NH4+].[OH-].[Na+]>CN(C)C=O>[OH:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[O:5][CH:6]([CH3:11])[CH2:7][CH2:8][C:9]1[NH:17][N:16]=[N:15][N:10]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 19844749HCID 19844749, compound

Product 1

HCID 178441992HCID 178441992, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5.9 g of 4-(3-hydroxyphenoxy)valeronitrile, 6.13 g of sodium azide and 5.0 g of ammonium chloride is heated with 30 ml of dry dimethylformamide at 140° C. for 20 hours. The reaction mixture is poured into ice, basified with 1N sodium hyroxide and extracted 2 times with warm ethyl acetate. The aqueous fraction is acidified with acetic acid. The product is filtered and washed with water to give crude product. Crystallization from ethyl acetate gives pure product which is used directly in the next step.

Workup

  1. additionThe reaction mixture is poured into ice
  2. extractionextracted 2 times with warm ethyl acetate
  3. filtrationThe product is filtered
  4. washwashed with water
  5. customto give crude product
  6. customCrystallization from ethyl acetate
  7. customgives pure product which

Sources & evidence

ORD record
ord-abedafc165624688ac33f387a06fa51b
Source dataset
uspto-grants-1989_10
Patent number
US04874769

Reaction notes

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