N-[(4-chlorophenyl)methylideneamino]-4-methylbenzenesulfonamide → 4-Chlorobenzaldehyde tosyl hydrazone sodium salt

HRID 1916023Notes

Reaction equation

HRID 1916023 reaction equation
[Na:1].[S:2]([NH:12][N:13]=[CH:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)(=[O:4])=[O:3]>CO>[Na:1].[Na:1].[S:2]([NH:12][N:13]=[CH:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

5

Reactant 2

HCID 333935N-[(4-chlorophenyl)methylideneamino]-4-methylbenzenesulfonamideHCID 5360545Sodium

Product 2

HCID 5360545SodiumHCID 866384034-Chlorobenzaldehyde tosyl hydrazone sodium saltYield 187.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A 1 M sodium methoxyde solution was prepared by adding sodium (423 mg, 18.39 mmol) to anhydrous methanol (19 ml) with external cooling. Once all of the metal was dissolved, 4-chlorobenzaldehyde tosyl hydrazone (5.39 g, 17.51 mmol) was added and the mixture was stirred until the solid was dissolved. After stirring for a further 15 min at room temperature the methanol was removed under reduced pressure at room temperature. 5.73 g of 4-chlorobenzaldehyde tosyl hydrazone sodium salt was obtained in the form of a white powder (99% of theory).

Workup

  1. dissolutionOnce all of the metal was dissolved
  2. dissolutionwas dissolved
  3. customwas removed under reduced pressure at room temperature

Sources & evidence

ORD record
ord-e04e3be6279d4fd3afe9a8ad36ca1770
Source dataset
uspto-grants-2013_12
Patent number
US08618023B2

Reaction notes

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