Hydrochloric Acid → 2,2,3,3,4,4,4-heptafluoro-N-[2-(cyanomethyl)phenyl]butanamide

HRID 35018

反応式

HRID 35018 の反応式
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][C:5]#[N:6].C(N(C(C)C)CC)(C)C.[F:20][C:21]([F:32])([C:28]([F:31])([F:30])[F:29])[C:22]([F:27])([F:26])[C:23](Cl)=[O:24].Cl>ClCCl>[F:26][C:22]([F:27])([C:21]([F:20])([F:32])[C:28]([F:29])([F:30])[F:31])[C:23]([NH:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][C:5]#[N:6])=[O:24]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 67810Heptafluorobutyryl ChlorideHCID 76307Phenylglycine nitrileHCID 81531Diisopropylethylamine

生成物 1

HCID 142538052,2,3,3,4,4,4-heptafluoro-N-[2-(cyanomethyl)phenyl]butanamide収率 95%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A mixture of 2-aminobenzylcyanide (15 g) [Rousseau et al., JACS 72, 3047 (1950)], diisopropylethylamine (16 g) and dichloromethane (400 mL) was cooled in an ice bath under a nitrogen atmosphere. Heptafluorobutyryl chloride (28.9 g) in dichloromethane (100 mL) was added dropwise and the reaction was left to warm gradually to room temperature overnight. A 10% aqueous HCl solution was added and the organic phase was separated and dried over MgSO4. After filtration and concentration with a rotary evaporator, the crude, orange oil (42 g) was purified by high pressure liquid chromatography to give 35.4 g of 2,2,3,3,4,4,4-heptafluoro-N-[2-(cyanomethyl)phenyl]butanamide as a white solid, m.p. 76°-79° C.

後処理

  1. temperaturewas cooled in an ice bath under a nitrogen atmosphere
  2. waitthe reaction was left
  3. customthe organic phase was separated
  4. dry with materialdried over MgSO4
  5. filtrationAfter filtration and concentration
  6. customwith a rotary evaporator
  7. customthe crude, orange oil (42 g) was purified by high pressure liquid chromatography

出典と根拠

ORDレコード
ord-66d1551a95aa45a89c0c098e44838954
出典データセット
uspto-grants-1988_08
特許番号
US04764623

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