Hydrazine hydrate (1:1) → Methyl 2-chloro-3-hydrazinocarbonyl-4-methylsulfonylbenzoate

HRID 1276131Notes

Reaction equation

HRID 1276131 reaction equation
[Cl:1][C:2]1[C:11]([C:12](Cl)=[O:13])=[C:10]([S:15]([CH3:18])(=[O:17])=[O:16])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].O.[NH2:20][NH2:21]>C(Cl)Cl>[Cl:1][C:2]1[C:11]([C:12]([NH:20][NH2:21])=[O:13])=[C:10]([S:15]([CH3:18])(=[O:17])=[O:16])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 18517408Methyl 2-chloro-3-chlorocarbonyl-4-methylsulfonylbenzoate

Product 1

HCID 22114944Methyl 2-chloro-3-hydrazinocarbonyl-4-methylsulfonylbenzoateYield 39.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

At room temperature, 3.11 g (10 mmol) of methyl 2-chloro-3-chloroformyl-4-methylsulfonylbenzoate in 50 ml of methylene chloride were added dropwise to 1.0 g (20 mmol) of hydrazine hydrate in 30 ml of methylene chloride. The reaction mixture was stirred at room temperature for 1 hour and then washed with water, dried and concentrated. 1.2 g (39% of theory) of methyl 2-chloro-3-hydrazinocarbonyl-4-methylsulfonylbenzoate were obtained.

Workup

  1. washwashed with water
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-989007f211bf4a5591f723e78aacc1b4
Source dataset
uspto-grants-2000_12
Patent number
US06165944

Reaction notes

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