Dimethylamine → 3-[(Dimethylamino)diazenyl]-5-(tert-butyl)selenophene-2-carbonitrile

HRID 1097192Notes

Reaction equation

Cl[C:2]([C:6]([CH3:9])([CH3:8])[CH3:7])=[CH:3][C:4]#[N:5].[Se-2:10].[Na+].[Na+].Cl[CH2:14][C:15]#[N:16].[N:17]([O-])=O.[Na+].[CH3:21][NH:22][CH3:23]>>[NH2:5][C:4]1[CH:3]=[C:2]([C:6]([CH3:9])([CH3:8])[CH3:7])[Se:10][C:14]=1[C:15]#[N:16].[CH3:21][N:22]([N:17]=[N:5][C:4]1[CH:3]=[C:2]([C:6]([CH3:9])([CH3:8])[CH3:7])[Se:10][C:14]=1[C:15]#[N:16])[CH3:23]

Participants

Reactant 5

HCID 674Dimethylamine

HCID 7856Chloroacetonitrile

HCID 73973Sodium selenide

HCID 27356613-Chloro-4,4-dimethylpent-2-enenitrile

HCID 23668193Sodium Nitrite

Product 2

HCID 497839913-[(Dimethylamino)diazenyl]-5-(tert-butyl)selenophene-2-carbonitrile

HCID 595472203-Amino-5-(tert-butyl)selenophene-2-carbonitrile

Procedure

The 3-amino-5-(tert-butyl)selenophene-2-carbonitrile is prepared starting from the 3-chloro-4,4-dimethylpent-2-enenitrile, sodium selenide and chloroacetonitrile, which on diazotization with sodium nitrite followed by treatment with dimethylamine gave the required 3-[(dimethylamino)diazenyl]-5-(tert-butyl)selenophene-2-carbonitrile (compound 11).

Sources & evidence

ORD record: ord-27fbbf47bc8146bebf8e64af7fa00325
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143237B2

Reaction notes

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