Triethylamine → HCID 67369848, compound

HRID 1873640Notes

Reaction equation

HRID 1873640 reaction equation
Cl[C:2](=[C:6]([C:9]#[N:10])[C:7]#[N:8])[CH:3]([CH3:5])[CH3:4].[Cl:11][C:12]1[C:13]([NH:19][NH2:20])=[N:14][CH:15]=[C:16]([Cl:18])[CH:17]=1.C(N(CC)CC)C>C1COCC1>[NH2:8][C:7]1[N:19]([C:13]2[C:12]([Cl:11])=[CH:17][C:16]([Cl:18])=[CH:15][N:14]=2)[N:20]=[C:2]([CH:3]([CH3:5])[CH3:4])[C:6]=1[C:9]#[N:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6009663,5-Dichloro-2-hydrazinylpyridineHCID 23513711(1-Chloro-2-methylpropylidene)propanedinitrile

Product 1

HCID 67369848HCID 67369848, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (1-chloro-2-methylpropylidene)methane-1,1-dicarbonitrile (35.6 g, 230 mmole) in THF (875 mL) was treated with 3,5-dichloropyridylhydrazine (40.9 g, 230 mmole) followed by triethylamine (23 g, 230 mmole). The reaction was then heated to reflux for 18 hours. The reaction was then cooled to room temperature and partitioned between EtOAc (1 L) and 1M aqueous NaOH (500 mL). The aqueous layer was extracted with EtOAc (2×500 mL), and the combined organic layers were washed with 10% citric acid (500 mL), saturated aqueous NaHCO3 (750 mL). The organic layer was dried (MgSO4), filtered, and concentrated under reduced pressure to yield the desired product (56 g, 82% yield).

Workup

  1. temperatureThe reaction was then heated
  2. temperatureto reflux for 18 hours
  3. custompartitioned between EtOAc (1 L) and 1M aqueous NaOH (500 mL)
  4. extractionThe aqueous layer was extracted with EtOAc (2×500 mL)
  5. washthe combined organic layers were washed with 10% citric acid (500 mL), saturated aqueous NaHCO3 (750 mL)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-27e31564d1e043f3b8baab56ac90d458
Source dataset
uspto-grants-2012_11
Patent number
US08304418B2

Reaction notes

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