tert-Butyl isocyanate → HCID 20147147, compound

HRID 569469Notes

Reaction equation

HRID 569469 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([OH:13])=[N:11][N:10]=[C:9]2[CH3:14])=[N:6][CH:7]=1.[C:15]([N:19]=[C:20]=[O:21])([CH3:18])([CH3:17])[CH3:16].C[O-].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([O:13][C:20]([NH:19][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:21])=[N:11][N:10]=[C:9]2[CH3:14])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 62412tert-Butyl isocyanateHCID 10942334Sodium MethoxideHCID 178434139HCID 178434139, compound

Product 1

HCID 20147147HCID 20147147, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

19.6 g (0.09 mol) of 4-(5-chloropyridin-2-yl)-5-hydroxy-3-methyl-1,2,4-triazole are suspended in 600 ml of absolute tetrahydrofuran. The mixture is heated to boiling and 20 g (0.2 mol) of tert-butylisocyanate are added, the mixture is heated for 10 minutes and 4 ml of a 5% methanolic sodium methoxide solution are added to the reaction mixture. It is then stirred for 24 hours under reflux conditions, then the suspension is concentrated and the residue is dissolved in methylene chloride and the insoluble components are removed by suction filtering. The organic phase is washed successively with 2 N hydrochloric acid, with sodium hydrogen carbonate solution and with water, dried with magnesium sulphate and evaporated in vacuo. After the addition of ether, 25 g (87% of theory) of the title compound were isolated in the form of crystals, m.p. 132°-134° C.

Workup

  1. additionare added
  2. temperaturethe mixture is heated for 10 minutes
  3. concentrationthe suspension is concentrated
  4. dissolutionthe residue is dissolved in methylene chloride
  5. customthe insoluble components are removed by suction
  6. filtrationfiltering
  7. washThe organic phase is washed successively with 2 N hydrochloric acid, with sodium hydrogen carbonate solution and with water
  8. dry with materialdried with magnesium sulphate
  9. customevaporated in vacuo
  10. additionAfter the addition of ether, 25 g (87% of theory) of the title compound
  11. customwere isolated in the form of crystals, m.p. 132°-134° C.

Sources & evidence

ORD record
ord-20482f041af84ed5a88ec610b4dfd52d
Source dataset
uspto-grants-1988_03
Patent number
US04732900

Reaction notes

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