Isopropanol → 3-Amino-2-cyano-3-isopropoxy-2-propenenitrile

HRID 1439333Notes

Reaction equation

[C:1]([C-:3]([C:6]#[N:7])[C:4]#[N:5])#[N:2].[K+].CS(O)(=O)=O.[CH:14]([OH:17])([CH3:16])[CH3:15]>>[NH2:2][C:1]([O:17][CH:14]([CH3:16])[CH3:15])=[C:3]([C:6]#[N:7])[C:4]#[N:5]

Participants

Reactant 3

HCID 3776Isopropanol

HCID 6395Methanesulfonic Acid

HCID 10964525Potassium Tricyanomethanide

Product 1

HCID 213968063-Amino-2-cyano-3-isopropoxy-2-propenenitrile

Procedure

In the manner of Example V A, 129.2 g of potassium tricyanomethanide and 1000 ml of isopropanol were treated with 65 ml (96 g) of methanesulfonic acid to yield 104 g of 3-amino-2-cyano-3-isopropoxy-2-propenenitrile, which was used as an intermediate without further purification. The ir spectrum was consistent with the assigned structure.

Sources & evidence

ORD record: ord-ebcaab2312b84e17a3ab42eb93a35b89
Source dataset: uspto-grants-1977_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04059433

Reaction notes

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