Hydrochloric Acid → 2,2,3,3,4,4,5,5,5-nonafluoro-N-[4-(cyanomethyl)phenyl]pentanamide

HRID 35022

Reaction equation

HRID 35022 reaction equation
[F:1][C:2]([F:16])([C:6]([F:15])([F:14])[C:7]([F:13])([F:12])[C:8]([F:11])([F:10])[F:9])[C:3]([OH:5])=O.C(OC#C)C.[NH2:22][C:23]1[CH:31]=[CH:30][C:26]([CH2:27][C:28]#[N:29])=[CH:25][CH:24]=1.Cl>C(OCC)(=O)C>[F:16][C:2]([F:1])([C:6]([F:15])([F:14])[C:7]([F:13])([F:12])[C:8]([F:11])([F:10])[F:9])[C:3]([NH:22][C:23]1[CH:31]=[CH:30][C:26]([CH2:27][C:28]#[N:29])=[CH:25][CH:24]=1)=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 61239Ether, ethyl ethynylHCID 75921Perfluoropentanoic acidHCID 770004-Aminophenylacetonitrile

Product 1

HCID 142538082,2,3,3,4,4,5,5,5-nonafluoro-N-[4-(cyanomethyl)phenyl]pentanamideYield 53%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Perfluorovaleric acid (10 g), ethoxyacetylene (12.3 g) and ethyl acetate (175 mL) were stirred overnight at room temperature under a nitrogen atmosphere. 4-Aminobenzylcyanide (5.57 g) was added and the resulting mixture was allowed to stir at room temperature for 24 hours. The reaction mixture was cooled in ice and 10% aqueous HCl solution was added until a precipitate formed. The solid was collected and washed with water and hexane, sequentially, and dried in vacuo to yield 7.4 g (53%) of 2,2,3,3,4,4,5,5,5-nonafluoro-N-[4-(cyanomethyl)phenyl]pentanamide as a tan solid, m.p. 126°-128° C.

Workup

  1. temperatureThe reaction mixture was cooled in ice
  2. customformed
  3. customThe solid was collected
  4. washwashed with water and hexane
  5. customsequentially, and dried in vacuo

Sources & evidence

ORD record
ord-f2b749b3013a4f95b6d4602cc7baf859
Source dataset
uspto-grants-1988_08
Patent number
US04764623

Linked notes

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