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Tripropylamine → 4-Amino-6-cyclohexanecarboxamidoquinazoline

HRID 354857
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 354857
Cl.[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH2:13])[CH:11]=2)[N:6]=[CH:5][N:4]=1.C(N(CCC)CCC)CC.[CH:24]1([C:30](Cl)=[O:31])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>N1C=CC=CC=1>[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:13][C:30]([CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)=[O:31])[CH:11]=2)[N:6]=[CH:5][N:4]=1
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Komponenten

5

Edukt 3

HCID 7616TripropylamineHCID 75938Cyclohexanecarbonyl chlorideHCID 202660864,6-Diaminoquinazoline hydrochloride

Produkt 1

HCID 130604644-Amino-6-cyclohexanecarboxamidoquinazolineAusbeute 56,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A mixture of 4,6-diaminoquinazoline hydrochloride (12 g) and tripropylamine (31.7 g) in dry pyridine (120 ml) was stirred in an ice-bath for 1 hour. Cyclohexanecarbonyl chloride (12.1 g) was added dropwise during 4 hours and 20 minutes to the mixture at 70° C. The mixture was stirred for additional 1 hour at 5° C. Crushed ice was added to the reaction mixture. The mixture was stirred for 1 hour and concentrated under reduced pressure. After addition of water, the mixture was adjusted to pH 8 with sodium hydrogen carbonate to give precipitates which were separated by filtration, washed with water and dried. The precipitates were dissolved in a mixture of chloroform and methanol under heating. Insoluble materials were removed by filtration. The filtrate was concentrated under reduced pressure to give crystalline 4-amino-6-cyclohexanecarboxamidoquinazoline (9.25 g).

Aufarbeitung

  1. stirringThe mixture was stirred for additional 1 hour at 5° C
  2. additionCrushed ice was added to the reaction mixture
  3. stirringThe mixture was stirred for 1 hour
  4. concentrationconcentrated under reduced pressure
  5. additionAfter addition of water
  6. customto give
  7. customprecipitates which
  8. customwere separated by filtration
  9. washwashed with water
  10. customdried
  11. dissolutionThe precipitates were dissolved in a mixture of chloroform and methanol
  12. temperatureunder heating
  13. customInsoluble materials were removed by filtration
  14. concentrationThe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8e1332a6bb3c425e804c2101b5d49e5d
Quelldatensatz
uspto-grants-1983_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04377580

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