Triethylamine → HCID 20443118, compound

HRID 1632487Notes

Reaction equation

HRID 1632487 reaction equation
Cl[C:2]1[O:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[CH3:11][C:12]([CH3:18])([CH2:15][NH:16][NH2:17])[C:13]#[N:14].C(N(CC)CC)C>O1CCOCC1>[O:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[N:16]([CH2:15][C:12]([CH3:18])([CH3:11])[C:13]#[N:14])[NH2:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 119862-ChlorobenzoxazoleHCID 20443124HCID 20443124, compound

Product 1

HCID 20443118HCID 20443118, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 2,2-dimethyl-2-cyanoacetaldehyde (9.4 g.) in ethanol (100 ml.) is added dropwise to a solution of hydrazine hydrate (40 g.) in ethanol (400 ml.), heated under reflux over a period of 3 hours. The solvent and excess of reagent are removed in vacuo to give 2,2-dimethyl-2-cyanoacetaldehyde hydrazone. This is dissolved in ethanol (100 ml.) and treated at room temperature with sodium borohydride (3.7 g.). The reaction mixture is stirred for two hours, acidified with acetic acid to pH 5, diluted with water and extracted with methylene chloride. The organic phase is dried and concentrated in vacuo to give 2,2-dimethyl-3-hydrazinopropanenitrile. A solution of 2-chlorobenzoxazole (15.3 g.) in dioxane (150 ml.) is added dropwise at 0° C. to a solution of 2,2-dimethyl-3-hydrazinopropanenitrile (11.3 g.) and triethylamine (10.1 g.) in dioxane (400 ml.). Stirring is continued overnight at room temperature. The precipitate is filtered and the filtrate concentrated in vacuo. The residue is washed with water and crystallized to give 3-[1-(2-benzoxazolyl) hydrazino)-2,2-dimethylpropanenitrile.

Workup

  1. filtrationThe precipitate is filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. washThe residue is washed with water
  4. customcrystallized

Sources & evidence

ORD record
ord-3d9a7d4fc25a437890348c4633bcba3b
Source dataset
uspto-grants-1984_10
Patent number
US04476137

Reaction notes

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