Triethylamine → N-{[5-(Methoxymethyl)-1,2,4-oxadiazol-3-yl]methyl}formamide

HRID 2351312Notes

Reaction equation

HRID 2351312 reaction equation
[CH:1]1([C:4]2[O:8][N:7]=[C:6]([CH2:9][N+:10]#[C-:11])[N:5]=2)CC1.C1([C:15]2[O:19]N(C)C(NC=O)N=2)CC1.C(N(CC)CC)C.[O:31]=P(Cl)(Cl)Cl>C(Cl)Cl.O>[CH:11]([NH:10][CH2:9][C:6]1[N:5]=[C:4]([CH2:1][O:19][CH3:15])[O:8][N:7]=1)=[O:31]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 107493421,2,4-Oxadiazole, 5-cyclopropyl-3-(isocyanomethyl)-HCID 867411005-Cyclopropyl-3-formylamino-methyl1,2,4-oxadiazole

Product 1

HCID 14460545N-{[5-(Methoxymethyl)-1,2,4-oxadiazol-3-yl]methyl}formamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

5-Cyclopropyl-3-isocyanomethyl-1,2,4-oxadiazole 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 Na (60 mmol) in H2O (50 ml) was added. The mixture was heated to room temperature, 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. customevaporated in vacuo
  3. additionThe residue was treated with ether
  4. customdecanted
  5. customthe solution was evaporated

Sources & evidence

ORD record
ord-19957d3343934eab8021677ad444dc5c
Source dataset
uspto-grants-1989_10
Patent number
US04873244

Reaction notes

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