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5-methyl-1H-pyrazole-3-carboxylic acid → HCID 53972348、化合物

HRID 1763936
ノート
印刷プレビュー

反応式

HRID 1763936 の反応式
ClC(OCC)=O.[CH3:7][C:8]1[NH:12][N:11]=[C:10]([C:13]([OH:15])=O)[CH:9]=1.Cl.[NH2:17][CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([O:30]CC)=[O:29])=[CH:22][CH:21]=1.[OH-].[Na+]>C(O)C.C(N(CC)CC)C.O1CCCC1>[CH3:7][C:8]1[NH:12][N:11]=[C:10]([C:13]([NH:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[CH:22][CH:21]=2)=[O:15])[CH:9]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 98225-methyl-1H-pyrazole-3-carboxylic acidHCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 20463439Ethyl 3-[4-(2-aminoethyl)phenyl]propanoate--hydrogen chloride (1/1)

生成物 1

HCID 53972348HCID 53972348、化合物収率 22%

試薬・触媒・溶媒 3

HCID 702
Ethanol
溶媒
HCID 8028Tetrahydrofuran溶媒
HCID 8471Triethylamine溶媒2 回

実験手順

1.27 ml. triethylamine and 0.85 ml. ethyl chloroformate are added at -10° C. to a solution of 1.12 g. of 5-methylpyrazole-3-carboxylic acid in 25 ml. anhydrous tetrahydrofuran. After 15 minutes, a further 1.27 ml. triethylamine is added and then 2.57 g. ethyl β-[4-(2-aminoethyl)-phenyl]-propionate hydrochloride. The reaction mixture is stirred for 1 hour at +20° C., filtered with suction and the filtrate is evaporated and the residue taken up in methylene chloride. After extraction with 2N hydrochloric acid, 2N aqueous sodium hydroxide solution and neutralization, the solution is dried and evaporated. The crude ester thus obtained is heated under reflux for 1 hour with 0.6 g. sodium hydroxide in 30 ml. ethanol. After cooling, the precipitated sodium salt is filtered off with suction, dissolved in water and carefully acidified. The precipitate obtained is filtered off and recrystallized from 20% ethanol. There is obtained β-{4-[2-(5-methylpyrazole- 3-carboxamido)-ethyl]-phenyl}-propionic acid in a yield of 22% of theory; m.p. 202°-205° C.

後処理

  1. filtrationfiltered with suction
  2. customthe filtrate is evaporated
  3. extractionAfter extraction with 2N hydrochloric acid, 2N aqueous sodium hydroxide solution and neutralization
  4. customthe solution is dried
  5. customevaporated
  6. customThe crude ester thus obtained
  7. temperatureis heated
  8. temperatureunder reflux for 1 hour with 0.6 g
  9. temperatureAfter cooling
  10. filtrationthe precipitated sodium salt is filtered off with suction
  11. dissolutiondissolved in water
  12. customThe precipitate obtained
  13. filtrationis filtered off
  14. customrecrystallized from 20% ethanol

出典と根拠

ORDレコード
ord-116d710299ad415ea1bfed0e46dd2a20
出典データセット
uspto-grants-1978_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04113871

反応ノート

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