Aniline → Cyclohexanecarboxamide, N-(2-bromo-4-nitrophenyl)-1,2,2,3,3,4,4,5,5,6,6-undecafluoro-

HRID 981833

Reaktionsgleichung

Reaktionsgleichung von HRID 981833
[F:1][C:2]1([C:18](F)=[O:19])[C:7]([F:9])([F:8])[C:6]([F:11])([F:10])[C:5]([F:13])([F:12])[C:4]([F:15])([F:14])[C:3]1([F:17])[F:16].C(N(CC)CC)C.[Br:28][C:29]1[CH:35]=[C:34]([N+:36]([O-:38])=[O:37])[CH:33]=[CH:32][C:30]=1[NH2:31].NC1C=CC=CC=1>C(OCC)C>[Br:28][C:29]1[CH:35]=[C:34]([N+:36]([O-:38])=[O:37])[CH:33]=[CH:32][C:30]=1[NH:31][C:18]([C:2]1([F:1])[C:3]([F:16])([F:17])[C:4]([F:14])([F:15])[C:5]([F:13])([F:12])[C:6]([F:11])([F:10])[C:7]1([F:9])[F:8])=[O:19]

Komponenten

6

Edukt 4

HCID 6115AnilineHCID 8471TriethylamineHCID 25840Benzenamine, 2-bromo-4-nitro-HCID 2776044Cyclohexanecarbonyl fluoride, 1,2,2,3,3,4,4,5,5,6,6-undecafluoro-

Produkt 1

HCID 163772Cyclohexanecarboxamide, N-(2-bromo-4-nitrophenyl)-1,2,2,3,3,4,4,5,5,6,6-undecafluoro-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

1,2,2,3,3,4,4,5,5,6,6-Undecafluorocyclohexanecarbonyl fluoride estimated to be of 60% purity (10.9 grams; 0.02 mole) and triethylamine (2 grams; 0.02 mole) were placed in 25 ml of diethyl ether. 2-Bromo-4-nitroaniline (11.35 grams; 0.02 mole) in 75 ml of diethyl ether was added dropwise at ambient temperature of about 25° C. The reaction mixture was then stirred for 11/2 hours. TLC showed no remaining aniline starting material. The reaction mixture was washed with water three times and with dilute sodium bicarbonate solution once, and thereafter dried. The solvent was then removed by evaporation. The product residue was chromatographed on silica gel HPLC with ethyl acetate:hexane 1:5, which yielded 14.5 grams of product containing occluded solvent. It was recrystallized from hexane and air dried, yielding 5.0 grams (48%) of purified product melting at 98°-101° C. An additional 1 gram was obtained from the mother liquor for a total yield of 57%.

Aufarbeitung

  1. washThe reaction mixture was washed with water three times and with dilute sodium bicarbonate solution once
  2. customdried
  3. customThe solvent was then removed by evaporation
  4. customThe product residue was chromatographed on silica gel HPLC with ethyl acetate:hexane 1:5, which

Quellen und Nachweise

ORD-Eintrag
ord-84869bb457674cf6a3f33ad4ae3b9074
Quelldatensatz
uspto-grants-1991_02
Patentnummer
US04992471

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