Triethylamine → HCID 131723365, compound

HRID 2227446Notes

Reaction equation

HRID 2227446 reaction equation
C(N(CC)CC)C.Cl.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][NH2:17])=[CH:12][CH:11]=1.[Cl:18][C:19]1[CH:20]=[N:21][CH:22]=[C:23]([Cl:28])[C:24]=1[C:25](Cl)=[O:26]>C1COCC1>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]([C:25]([C:24]2[C:23]([Cl:28])=[CH:22][N:21]=[CH:20][C:19]=2[Cl:18])=[O:26])[NH2:17])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 115720223,5-Dichloropyridine-4-carbon chloride

Product 1

HCID 131723365HCID 131723365, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Triethylamine (1.40 mL, 1.02 g, 10.1 mmol) was added to a suspension of 4-chlorophenylhydrazine hydrochloride (1.83 g, 98%, 10.0 mmol) in THF (75 mL). The mixture was stirred under nitrogen at room temperature for 2.75 h. More triethylamine (3.0 mL, 21.6 mmol) was added followed by dropwise addition of a solution of freshly-prepared 3,5-dichloropyridine-4-carbonyl chloride (10.0 mmol) in THF (20 mL). After stirring overnight, the reaction mixture was concentrated under reduced pressure. The residue was partitioned between ethyl acetate (100 mL) and water (50 mL). The layers were shaken together and allowed to separate. The organic phase was dried (Na2SO4) and concentrated, leaving 3.04 g of a tan solid, mp 201-203.5° C. Recrystallized from ethyl acetate/cyclohexane and then from ethanol furnished crystals which melted at 206-207.5° C.

Workup

  1. stirringAfter stirring overnight
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe residue was partitioned between ethyl acetate (100 mL) and water (50 mL)
  4. stirringThe layers were shaken together
  5. customto separate
  6. dry with materialThe organic phase was dried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-68c9ac8f2fc04ff8b29cbf5e4548d782
Source dataset
uspto-grants-2002_07
Patent number
US06413992B1

Reaction notes

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