5-Bromo-4-methylthiophene-2-carbonitrile → 5(2-methylspiro[2H-3,1-benzoxazine-4,1'-cyclohexane]-6-yl)-4-methyl-2-thiophenecarbonitrile

HRID 277860

Reaktionsgleichung

Reaktionsgleichung von HRID 277860
[CH3:1][C:2]1[O:17][C:11]2([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[C:5]2[CH:6]=[C:7](Br)[CH:8]=[CH:9][C:4]=2[N:3]=1.Br[C:19]1[S:23][C:22]([C:24]#[N:25])=[CH:21][C:20]=1[CH3:26]>>[CH3:1][CH:2]1[O:17][C:11]2([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[C:5]2[CH:6]=[C:7]([C:19]3[S:23][C:22]([C:24]#[N:25])=[CH:21][C:20]=3[CH3:26])[CH:8]=[CH:9][C:4]=2[NH:3]1

Komponenten

3

Edukt 2

HCID 219862345-Bromo-4-methylthiophene-2-carbonitrileHCID 234355862-methyl-6-bromospiro[4H-3,1-benzoxazine-4,1'-cyclohexane]

Produkt 1

HCID 234356035(2-methylspiro[2H-3,1-benzoxazine-4,1'-cyclohexane]-6-yl)-4-methyl-2-thiophenecarbonitrile

Versuchsvorschrift

The title compound was prepared according to the procedure for Example 13 from 2-methyl-6-bromospiro[4H-3,1-benzoxazine-4,1′-cyclohexane] and 5-bromo-4-methyl-2-thiophenecarbonitrile. A brown solid: 1H-NMR (DMSO-d6) δ 7.78 (s, 1H), 7.17 (d, 1H, J=1.8 Hz), 7.14 (dd, 1H, J=8.4, 2.2 Hz), 6.64 (s, 1H), 6.63 (d, 1H, J=8.2 Hz), 4.74 (m, 1H), 2.26 (s, 3H), 2.14 (m, 1H), 1.87 (m, 1H), 1.4-1.7 (m, 8H), 1.31 (d, 3H, J=5.3 Hz); MS (ESI) m/z 337 [M−H]−.

Quellen und Nachweise

ORD-Eintrag
ord-54e70351894545c7a9ebe4d890f4dc84
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06358948B1

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