تفاعل #2468023

ord-bd97b84e6d7045a19546339bbf3e0cd5

معادلة التفاعل

CCOC(=O)C(=N)NO
ethyl 2-(hydroxyamino)-2-iminoacetate
CCOC(OCC)OCC
triethylorthoformate
CCOC(=O)c1ncon1
title compound
المردود 83.7%
CCOC(=O)c1ncon1
Ethyl 1,2,4-oxadiazole-3-carboxylate
المردود 83.7%

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةIt was heated for 90 minutes
  2. 2
    تركيزThe reaction mixture was concentrated under reduced pressure
  3. 3
    workup.DISSOLUTIONthe residue dissolved in chloroform
  4. 4
    غسيلThe resulting organic layer was washed with aqueous hydrochloric acid 2N (2×80 mL), aqueous sodium bicarbonate 4% (1×80 mL) and water (2×80 mL), it
  5. 5
    تجفيفwas dried over anhydrous sodium sulphate
  6. 6
    أخرىthe solvent removed under reduced pressure

الإجراء التجريبي

To a suspension of ethyl 2-(hydroxyamino)-2-iminoacetate (3 g, 22.71 mmol) in triethylorthoformate (14 mL, 84.08 mmol) was added boron trifluoride diethyl etherate (0.144 mL, 1.14 mmol). It was heated for 90 minutes. The reaction mixture was concentrated under reduced pressure and the residue dissolved in chloroform. The resulting organic layer was washed with aqueous hydrochloric acid 2N (2×80 mL), aqueous sodium bicarbonate 4% (1×80 mL) and water (2×80 mL), it was dried over anhydrous sodium sulphate and the solvent removed under reduced pressure to yield the title compound (2.70 g, 79%) as a yellow oil.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08258122B2uspto-grants-2012_09