Lithium Hydroxide → HCID 90412415, compound

HRID 2170837Notes

Reaction equation

HRID 2170837 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][NH2:9])=[C:4]([CH3:10])[CH:3]=1.[Li+].[OH-].[O:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[C:18](Cl)=[O:19]>CCOCC.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][NH:9][C:18]([C:14]2[O:13][CH:17]=[CH:16][CH:15]=2)=[O:19])=[C:4]([CH3:10])[CH:3]=1

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 682422-Furancarbonyl chlorideHCID 587842HCID 587842, compound

Product 1

HCID 90412415HCID 90412415, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a suspension of 1-(4-chloro-2-methylphenyl)hydrazine as the hydrochloride salt (96 mg, 0.5 mmol) in Et2O (10 mL) was added a 2 N solution of LiOH (3 mL), and the resulting mixture was stirred for 15 minutes. After the system became homogenous, furan-2-carbonyl chloride was added, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was then diluted with water (100 mL) and extracted with EtOAc (70 mL). The organic layer was separated, washed with brine, and dried over Na2SO4. The crude material of N′-(4-chloro-2-methylphenyl)furan-2-carbohydrazide obtained after the removal of the solvent was used in the next step without further purification.

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. extractionextracted with EtOAc (70 mL)
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-e8602f618a184b95891c21acba6c0fdb
Source dataset
uspto-grants-2015_06
Patent number
US09051309B2

Reaction notes

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