Triethylamine → 1,2,4-Oxadiazole, 5-cyclopropyl-3-(isocyanomethyl)-

HRID 2291267Notes

Reaction equation

HRID 2291267 reaction equation
[CH:1]1([C:4]2[O:8][N:7](C)[CH:6](NC=O)[N:5]=2)[CH2:3][CH2:2]1.[CH2:13]([N:15](CC)[CH2:16]C)C.O=P(Cl)(Cl)Cl>C(Cl)Cl.O>[CH:1]1([C:4]2[O:8][N:7]=[C:6]([CH2:16][N+:15]#[C-:13])[N:5]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 867411005-Cyclopropyl-3-formylamino-methyl1,2,4-oxadiazole

Product 1

HCID 107493421,2,4-Oxadiazole, 5-cyclopropyl-3-(isocyanomethyl)-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 5-cyclopropyl-3-formylamino-methyl-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 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-515aba5a36724bcc921f57a49355222a
Source dataset
uspto-grants-1989_01
Patent number
US04795749

Reaction notes

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