tert-Butanol → HCID 18382719, compound

HRID 1030096Notes

Reaction equation

HRID 1030096 reaction equation
[C:1]([C:3]1[C:8]([CH3:9])=[CH:7][C:6]([CH3:10])=[CH:5][N:4]=1)#[N:2].[C:11](O)([CH3:14])([CH3:13])[CH3:12].[OH-:16].[Na+]>C(O)(=O)C.S(=O)(=O)(O)O>[CH3:12][C:11]([NH:2][C:1]([C:3]1[C:8]([CH3:9])=[CH:7][C:6]([CH3:10])=[CH:5][N:4]=1)=[O:16])([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 6386tert-ButanolHCID 14798Sodium HydroxideHCID 81672693,5-dimethylpyridine-2-carbonitrile

Product 1

HCID 18382719HCID 18382719, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
75 °C

Procedure

Stir a solution of 2-cyano-3,5-dimethylpyridine (20.3 g, 0.153 mol) in 100 mL of acetic acid and 20 mL of conc. sulfuric acid over 10 minutes. Add t-butanol (20 ml.) over an additional 15 minutes. Warm the solution to 75° C. and maintain for 30 minutes. Cool to room temperature and basify with 25% NaOH. Extract the product (3X) with ethyl acetate (600 mL). Combine the organic portions and wash (1X) with brine. Dry (Na2SO4), filter and concentrate in vacuo to produce the title compound as a yellowish oil (31.26 g).

Workup

  1. temperaturemaintain for 30 minutes
  2. temperatureCool to room temperature
  3. extractionExtract the product (3X) with ethyl acetate (600 mL)
  4. washCombine the organic portions and wash (1X) with brine
  5. dry with materialDry (Na2SO4)
  6. filtrationfilter
  7. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-80f665e243894c86a5c703c43e8bdadc
Source dataset
uspto-grants-1992_04
Patent number
US05104876

Reaction notes

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