Triethylamine → 3-Cyclopropyl-5-(isocyanomethyl)-1,2,4-oxadiazole

HRID 358957Notes

Reaction equation

HRID 358957 reaction equation
[CH:1]1([C:4]2[N:8]=[C:7]([CH2:9][NH:10][CH:11]=O)[O:6][N:5]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.O=P(Cl)(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl.O>[CH:1]1([C:4]2[N:8]=[C:7]([CH2:9][N+:10]#[C-:11])[O:6][N:5]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 14460538N-((3-Cyclopropyl-1,2,4-oxadiazol-5-yl)methyl)formamide

Product 1

HCID 229129243-Cyclopropyl-5-(isocyanomethyl)-1,2,4-oxadiazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 3-cyclopropyl-5-formylaminomethyl-1,2,4-oxadiazole (60 mmol) and triethylamine (176 mmol) in CH2Cl2 (100 ml) was charged dropwise with POCl3 (60 mmol) at 0° C. The mixture was then left for 30 minutes with stirring at 0° C. whereafter a solution of Na2CO3 (60 mmol) in H2O (50 ml) was added. The mixture was heated to room temperature, whereafter the organic phase was separated, dried and evaporated in vacuo. The residue was treated with ether, decanted and the solution was evaporated to give the title compound as an oil. The oil was processed without any further purification. The compound was characterized by its IR absorbtion band at 2160 cm-1.

Workup

  1. additionwas added
  2. customwas separated
  3. customdried
  4. customevaporated in vacuo
  5. additionThe residue was treated with ether
  6. customdecanted
  7. customthe solution was evaporated

Sources & evidence

ORD record
ord-69a94077d8d447eca6488a69b00559bb
Source dataset
uspto-grants-1991_03
Patent number
US04999354

Reaction notes

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