Cyclohexanone → 3,4-dihydro-6-(1,1-dimethylethyl)-8-iodospiro[2H-1,3-benzoxazine-2,1'-cyclohexane]

HRID 372835

Reaktionsgleichung

Reaktionsgleichung von HRID 372835
[NH2:1][CH2:2][C:3]1[CH:8]=[C:7]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:6]=[C:5]([I:13])[C:4]=1[OH:14].[C:15]1(=O)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.S([O-])([O-])(=O)=O.[Mg+2]>O1CCCC1>[CH3:12][C:9]([C:7]1[CH:6]=[C:5]([I:13])[C:4]2[O:14][C:15]3([CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[NH:1][CH2:2][C:3]=2[CH:8]=1)([CH3:11])[CH3:10]

Komponenten

5

Edukt 3

HCID 7967CyclohexanoneHCID 24083Sulfuric acid magnesium salt (1:1)HCID 1192862-Aminomethyl-4-t-butyl-6-iodophenol

Produkt 1

HCID 128578923,4-dihydro-6-(1,1-dimethylethyl)-8-iodospiro[2H-1,3-benzoxazine-2,1'-cyclohexane]Ausbeute 72,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 2-aminomethyl-4-(1,1-dimethylethyl)-6-iodophenol (1.5 g., 0.005 mole), cyclohexanone (0.5 g., 0.005 mole), and magnesium sulfate (0.5 g.) in tetrahydrofurane (50 ml.) is kept under nitrogen at 20°-25° C., for 16 hours. The magnesium sulfate is removed and the filtrate evaporated to dryness. The residue is crystallized from ethanol to obtain 3,4-dihydro-6-(1,1-dimethylethyl)-8-iodospiro[2H-1,3-benzoxazine-2,1'-cyclohexane] (1.4 g.), m.p. 112°-114° C.

Aufarbeitung

  1. customThe magnesium sulfate is removed
  2. customthe filtrate evaporated to dryness
  3. customThe residue is crystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-5aea0e76281a433ea39b979896e6e638
Quelldatensatz
uspto-grants-1978_05
Patentnummer
US04092414

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