Triethylamine → 2,2,3,3,4,4,4-heptafluoro-N-[4-(cyano)phenyl]butanamide

HRID 35020

反応式

HRID 35020 の反応式
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[F:17][C:18]([F:29])([C:22]([F:28])([F:27])[C:23]([F:26])([F:25])[F:24])[C:19](Cl)=[O:20]>ClCCl.Cl>[F:17][C:18]([F:29])([C:22]([F:27])([F:28])[C:23]([F:24])([F:25])[F:26])[C:19]([NH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1)=[O:20]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 133964-AminobenzonitrileHCID 67810Heptafluorobutyryl Chloride

生成物 1

HCID 142538062,2,3,3,4,4,4-heptafluoro-N-[4-(cyano)phenyl]butanamide収率 36.9%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

A mixture of 4-aminobenzonitrile (1.58 g), triethylamine (1.36 g), and dichloromethane (20 mL) was cooled in ice under a nitrogen atmosphere. To this mixture was added perfluorobutyryl chloride (3.11 g) in dichloromethane (10 mL) and the resulting mixture was allowed to warm to room temperature and was then stirred for three hours. The reaction mixture was diluted with HCl solution (1N, 50 mL) and the layers were partitioned in a separatory funnel. The organic phase was washed with a saturated brine solution, dried over MgSO4, filtered and concentrated with a rotary evaporator. The residue was dissolved in dichloromethane. Upon dilution with hexane the product precipitated to give 1.55 g of 2,2,3,3,4,4,4-heptafluoro-N-[4-(cyano)phenyl]butanamide, m.p. 116°-118° C.

後処理

  1. temperaturewas cooled in ice under a nitrogen atmosphere
  2. customthe layers were partitioned in a separatory funnel
  3. washThe organic phase was washed with a saturated brine solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated with a rotary evaporator
  7. dissolutionThe residue was dissolved in dichloromethane
  8. customUpon dilution with hexane the product precipitated

出典と根拠

ORDレコード
ord-fd7a1f957094494980469d14f25061e8
出典データセット
uspto-grants-1988_08
特許番号
US04764623

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