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Cyanamide → N-cyano-2,2-bis(fluoromethyl)-N'-methyl-6-nitro-2H-1-benzopyran-4-amidine

HRID 264840
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 264840
[F:1][CH2:2][C:3]1([CH2:20][F:21])[CH:8]=[C:7]([C:9](=S)[NH:10][CH3:11])[C:6]2[CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=[CH:16][C:5]=2[O:4]1.[I-].ClC1C=CC=C[N+]=1C.[N:31]#[C:32][NH2:33].[H-].[Na+]>O1CCCC1.C(N(CC)CC)C>[C:32]([NH:33][C:9]([C:7]1[C:6]2[CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=[CH:16][C:5]=2[O:4][C:3]([CH2:20][F:21])([CH2:2][F:1])[CH:8]=1)=[N:10][CH3:11])#[N:31]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 9864CyanamideHCID 24758Sodium hydrideHCID 1670692-Chloro-1-methylpyridinium iodideHCID 104033502,2-bis(fluoromethyl)-N-methyl-6-nitro-2H-1-benzopyran-4-carbothioamide

Produkt 1

HCID 19037066N-cyano-2,2-bis(fluoromethyl)-N'-methyl-6-nitro-2H-1-benzopyran-4-amidineAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 8028TetrahydrofuranLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A mixture of 84 mg of 2,2-bis(fluoromethyl)-N-methyl-6-nitro-2H-1-benzopyran-4-carbothioamide, 140 mg of 2-chloro-1-methylpyridinium iodide, 0.06 ml of triethylamine and 2 ml of dried tetrahydrofuran was refluxed with heating for 2 hours. After the reaction solution was cooled to room temperature, 42 mg of cyanamide and 38 mg of sodium hydride (60%) were added therein and the resultant mixture was refluxed with heating for 4 hours. Ice water was added therein and the mixture was extracted with methylene chloride. An organic layer was washed with water and dried, and the solvent was distilled. The obtained residue was purified according to silica gel column chromatography (developing solution, MeOH:CH2Cl2 =1:99). The resultant product was recrystallized by a mixed solvent of ethyl acetate and hexane to obtain 21.5 mg of N-cyano-2,2-bis(fluoromethyl)-N'-methyl-6-nitro-2H-1-benzopyran-4-amidine with a melting point of 259°-261° C.

Aufarbeitung

  1. temperaturewas refluxed
  2. temperaturewith heating for 2 hours
  3. temperaturewith heating for 4 hours
  4. extractionthe mixture was extracted with methylene chloride
  5. washAn organic layer was washed with water
  6. customdried
  7. distillationthe solvent was distilled
  8. customThe obtained residue was purified
  9. customThe resultant product was recrystallized by a mixed solvent of ethyl acetate and hexane

Quellen und Nachweise

ORD-Eintrag
ord-338aa32e1da14c8a85f2881eec108f73
Quelldatensatz
uspto-grants-1997_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05646308

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