Phosphorus oxychloride → Ethyl 6-chloropyridazine-3-carboxylate

HRID 1742581

反応式

HRID 1742581 の反応式
O[C:2]1[N:3]=[N:4][C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][CH:7]=1.OC1N=NC(C(O)=O)=CC=1.P(Cl)(Cl)([Cl:25])=O>>[Cl:25][C:2]1[N:3]=[N:4][C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][CH:7]=1

参加物

4

反応物 3

HCID 24813Phosphorus oxychlorideHCID 178469098HCID 178469098、化合物HCID 1785245006-hydroxypyridazine-3-carboxylic acid

生成物 1

HCID 10352425Ethyl 6-chloropyridazine-3-carboxylate

実験手順

Ethyl 3-hydroxypyridazine-6-carboxylate [22.00 g, 0.13 mol, prepared from 3-hydroxypyridazine-6-carboxylic acid according to the procedure of Libermann, D. and Rouaix, A. (Bull. Soc. Chim . Fr. 1959, 1793-1798)] and phosphorous oxychloride (122 mL, 1.31 mol) were heated at 110° C. (via an oil bath) for 1 h. The mixture was cooled and concentrated under reduced pressure, which removed the excess phosphorous oxychloride. The residue was dissolved into chloroform, cooled, and carefully washed with saturated sodium bicarbonate solution. The chloroform extract was dried (MgSO4) , filtered, concentrated and recrystallized from ethyl acetate-diisopropyl ether to afford ethyl 6-chloro-3-pyridazinecarboxylate as tan needles, mp 145°-150° C.

後処理

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated under reduced pressure, which
  3. customremoved the excess phosphorous oxychloride
  4. dissolutionThe residue was dissolved into chloroform
  5. temperaturecooled
  6. washcarefully washed with saturated sodium bicarbonate solution
  7. extractionThe chloroform extract
  8. dry with materialwas dried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customrecrystallized from ethyl acetate-diisopropyl ether

出典と根拠

ORDレコード
ord-778887a8504e4d1a94f4ea689e334cc7
出典データセット
uspto-grants-1994_08
特許番号
US05340808

関連ノート

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