Tetrahydrofuran → 2-chloro-benzoic acid N'-(5-bromo-pyridin-2-yl)hydrazide

HRID 2252317Notes

Reaction equation

HRID 2252317 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH2:9])=[N:6][CH:7]=1.C(N(CC)CC)C.C1COCC1.[Cl:22][C:23]1[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=1[C:25](Cl)=[O:26]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH:9][C:25](=[O:26])[C:24]2[CH:28]=[CH:29][CH:30]=[CH:31][C:23]=2[Cl:22])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 691102-Chlorobenzoyl chlorideHCID 115356995-Bromo-2-hydrazinopyridine

Product 1

HCID 692020042-chloro-benzoic acid N'-(5-bromo-pyridin-2-yl)hydrazideYield 85.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (5-bromo-pyridin-2-yl)-hydrazine (2.0 g, 10.6 mmol) and triethylamine (1.5 mL, 11.0 mmol) in 1:1 THF:CH2Cl2 (15 mL) was added 2-chlorobenzoyl chloride (1.34 mL, 10.6 mmol) and the resulting reaction stirred for 16 hours. The reaction was quenched with water (100 mL), the resulting solids filtered, and dried to give the title compound (2.96 g, 85%).

Workup

  1. customthe resulting reaction
  2. customThe reaction was quenched with water (100 mL)
  3. filtrationthe resulting solids filtered
  4. customdried

Sources & evidence

ORD record
ord-f14bd9ef1eda424fb69a28b9d5c11856
Source dataset
uspto-grants-2008_01
Patent number
US07321040B2

Reaction notes

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