Dimethylformamide → 1-amino-1H-pyrrole-2,4-dicarbonitrile

HRID 1972975Notes

Reaction equation

HRID 1972975 reaction equation
[C:1]([C:3]1[NH:4][CH:5]=[C:6]([C:8]#[N:9])[CH:7]=1)#[N:2].[H-].[Na+].C[N:13](C=O)C>>[NH2:13][N:4]1[CH:5]=[C:6]([C:8]#[N:9])[CH:7]=[C:3]1[C:1]#[N:2]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 5759051H-Pyrrole-2,4-dicarbonitrile

Product 1

HCID 552958981-amino-1H-pyrrole-2,4-dicarbonitrileYield 59%

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 2,4-dicyano-pyrrole (3.00 g, 25.6 mmol) in DMF (300 mL) was added sodium hydride (60% in mineral oil, 1.54 g, 38.4 mmol). The mixture was stirred for 15 min. Diphenylphosphinyl amino ester (8.96 g, 38.4 mmol) was added. The mixture was vigorously stirred while heating at 80° C. for 2 h and then cooled to rt. The mixture was filtered using DCM washings. The filtrate was concentrated to dryness to provide desired product (2.00 g, 59%). LTQ LC-MS: [M+H]+ 133.0, RT 0.96 min. The product was used in the next step without further purification.

Workup

  1. stirringThe mixture was vigorously stirred
  2. temperaturecooled to rt
  3. filtrationThe mixture was filtered
  4. concentrationThe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-9c5cf30baa6245c085bd67fd1f25733d
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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