Sodium Hydroxide → 1-Pyrimid-2-yl-4-(4-chloro-phenyl)pyrazolin-5-one

HRID 255494

反応式

HRID 255494 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11]CC)=O)=[CH:4][CH:3]=1.[CH3:14]OC(OC)N(C)C.[NH:22]([C:24]1[N:29]=[CH:28][CH:27]=[CH:26][N:25]=1)[NH2:23].[OH-].[Na+]>Cl.O>[N:25]1[CH:26]=[CH:27][CH:28]=[N:29][C:24]=1[N:22]1[C:9](=[O:11])[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[CH:14][NH:23]1

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 78373Dimethylformamide dimethyl acetalHCID 84177Ethyl (4-chlorophenyl)acetateHCID 3465582-Hydrazinylpyrimidine

生成物 1

HCID 135905371-Pyrimid-2-yl-4-(4-chloro-phenyl)pyrazolin-5-one収率 26.4%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒2 回HCID 962Water溶媒

実験手順

19.9 g (0.1 mole) of ethyl 4-chloro-phenylacetate are heated at 100° C. with 23.8 g (0.2 mole) of dimethylformamide dimethyl acetal for 5 hours. All the volatile constituents are then distilled off at this temperature under a waterpump vacuum. The oily residue, which essentially consists of ethyl α-dimethylaminomethylene-4-chlorophenylacetate, is dissolved, without further purification, in 140 ml of ethanol. 11 g (0.1 mole) of 2-hydrazinopyrimidine and 10 ml of concentrated hydrochloric acid are added. The mixture is heated under reflux for 5 hours, cooled to room temperature and, after addition of 9 g of concentrated sodium hydroxide solution, stirred at room temperature for 5 hours. After neutralization with dilute hydrochloric acid, the mixture is diluted with 1 liter of water. The crystals which have separated out are filtered off with suction, washed with water and dried in air. 7.2 g (26.4% of theory) of 1-pyrimid-2-yl-4-(4-chloro-phenyl)pyrazolin-5-one are obtained. Melting point: 190° to 191° C. (methanol).

後処理

  1. distillationAll the volatile constituents are then distilled off at this temperature under a waterpump vacuum
  2. dissolutionis dissolved, without further purification, in 140 ml of ethanol
  3. temperatureThe mixture is heated
  4. temperatureunder reflux for 5 hours
  5. customThe crystals which have separated out
  6. filtrationare filtered off with suction
  7. washwashed with water
  8. customdried in air

出典と根拠

ORDレコード
ord-e456f43b817c4adf98a2f02c0b14dc07
出典データセット
uspto-grants-1987_10
特許番号
US04698344

関連ノート

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