Pyrrolidine → [(1E)-2-Cyano-1-(pyrrolidin-1-yl)ethylidene]cyanamide

HRID 437856Notes

Reaction equation

HRID 437856 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:6]([N:8]=[C:9](OCC)[CH2:10][C:11]#[N:12])#[N:7]>O1CCCC1>[C:6]([N:8]=[C:9]([N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)[CH2:10][C:11]#[N:12])#[N:7]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 12272864Ethanimidic acid, N,2-dicyano-, ethyl ester

Product 1

HCID 12436750[(1E)-2-Cyano-1-(pyrrolidin-1-yl)ethylidene]cyanamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Pyrrolidine (2.07 g, 0.0292 m) is added to 4.00 g (0.0292 m) of an ice-cooled solution of ethyl N,2-dicyanoacetimidate in 80 ml of tetrahydrofuran and stirred for two hours at room temperature. The crude product is isolated and chromatographed in the same manner as that of Example 2. The tlc-pure crystalline product (4.80 g) is triturated with diethyl ether to give 4.00 g (84%), mp 45° C. Nmr and ir are consistent.

Sources & evidence

ORD record
ord-d80a32b693984bdc99761819cf4fd4c6
Source dataset
uspto-grants-1977_06
Patent number
US04032559

Reaction notes

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