Chloroacetonitrile → 3-Amino-4,5,6,7-tetrahydrobenzo[1,2-b]selenophene-2-carbonitrile

HRID 1097193

Reaktionsgleichung

Cl[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]=1[C:8]#[N:9].[Se-2:10].[Na+].[Na+].Cl[CH2:14][C:15]#[N:16].[OH-].[Na+]>>[NH2:9][C:8]1[C:3]2[CH2:4][CH2:5][CH2:6][CH2:7][C:2]=2[Se:10][C:14]=1[C:15]#[N:16]

Komponenten

Edukt 4

HCID 7856Chloroacetonitrile

HCID 14798Sodium Hydroxide

HCID 73973Sodium selenide

HCID 498409392-Chlorocyclohex-1-ene-1-carbonitrile

Produkt 1

HCID 595472123-Amino-4,5,6,7-tetrahydrobenzo[1,2-b]selenophene-2-carbonitrile

Versuchsvorschrift

The 3-amino-4,5,6,7-tetrahydrobenzo[1,2-b]selenophene-2-carbonitrile is prepared starting from 2-chlorocyclohex-1-enecarbonitrile, sodium selenide and chloroacetonitrile, which on treatment with aqueous sodium hydroxide gave the corresponding amide in good yield. Diazotization of the amine with sodium nitrite followed by treatment with iodomethane in presence of a base gave the required 3-methyl-6,7,8,9-tetrahydrobenzo[1,2-b]1,2,3-triazino-[4,5-d]-selenophen-4-one (compound 14).

Quellen und Nachweise

ORD-Eintrag: ord-c00d8f15095a451b8ea9a4115a04e0ff
Quelldatensatz: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08143237B2

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