Phenol → Phenyl 1-(4-Chlorophenyl)-1,4-dihydro-4-oxo-6-methylpyridazine-3-carboxylate

HRID 67265

反応式

HRID 67265 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13]([CH3:14])=[CH:12][C:11](=[O:15])[C:10]([C:16]([OH:18])=[O:17])=[N:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(O[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=O.C1(O)C=CC=CC=1>C1(C)C=CC=CC=1.CCCCCC.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13]([CH3:14])=[CH:12][C:11](=[O:15])[C:10]([C:16]([O:18][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:17])=[N:9]2)=[CH:4][CH:3]=1

参加物

8

反応物 4

HCID 996PhenolHCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 197225Fenridazon

生成物 1

HCID 9192006Phenyl 1-(4-Chlorophenyl)-1,4-dihydro-4-oxo-6-methylpyridazine-3-carboxylate収率 19.1%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1140Toluene溶媒2 回HCID 8058Hexane溶媒

実験手順

To an ice cooled suspension of 5.29 g (0.02 mol) 1-(4-chlorophenyl)-1,4-dihydro-4-oxo-6-methyl pyridazine-3-carboxylic Acid (see Example 12) and 2.02 g (0.02 mol) of triethylamine in 125 mol of toluene there is added dropwise 3.13 g (0.02 mol) of phenyl chloroformate. The suspension formed is stirred at room temperature for 15 minutes and to it there is added 1.88 g (0.02 mol) of phenol in 25 ml of toluene. The mixture is stirred at room temperature for 18 hrs. and to it there is added 100 ml of water. The suspension is stirred at room temperature for 2 hrs. and is poured into 800 ml of hexane. The suspension formed is stirred at room temperature for 3 hrs. and is vacuum filtered. The filter cake is slurried in 25 ml of toluene and is filtered. The filtrate is added to 150 ml of hexane and the suspension formed is stirred at room temperature for 2 hrs. The suspension is vacuum filtered and the filter cake air dried to afford 1.3 g (19% yield) of product, mp 140°-146° C.

後処理

  1. customThe suspension formed
  2. stirringThe mixture is stirred at room temperature for 18 hrs
  3. stirringThe suspension is stirred at room temperature for 2 hrs
  4. customThe suspension formed
  5. stirringis stirred at room temperature for 3 hrs
  6. filtrationfiltered
  7. filtrationis filtered
  8. additionThe filtrate is added to 150 ml of hexane
  9. customthe suspension formed
  10. stirringis stirred at room temperature for 2 hrs
  11. filtrationfiltered
  12. customthe filter cake air dried

出典と根拠

ORDレコード
ord-e9b5717f5d59430f8f2ec1312dd35dfb
出典データセット
uspto-grants-1982_08
特許番号
US04345934

関連ノート

読み込み中…