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

HRID 1097193Notes

Reaction equation

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]

Participants

Reactant 4

HCID 7856Chloroacetonitrile

HCID 14798Sodium Hydroxide

HCID 73973Sodium selenide

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

Product 1

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

Procedure

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).

Sources & evidence

ORD record: ord-c00d8f15095a451b8ea9a4115a04e0ff
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143237B2

Reaction notes

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