3-Nitrobenzaldehyde → HCID 67441320, compound

HRID 1800970Notes

Reaction equation

HRID 1800970 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[N+:12]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=O)([O-:14])=[O:13]>C(O)C>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]=[CH:18][C:17]2[CH:20]=[CH:21][CH:22]=[C:15]([N+:12]([O-:14])=[O:13])[CH:16]=2)=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 74493-NitrobenzaldehydeHCID 796174-(Methylsulfonyl)aniline

Product 1

HCID 67441320HCID 67441320, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-methanesulfonyl-phenylamine (5.6 g, 33 mmol) and 3-nitro-benzaldehyde (5.45 g, 36 mmol) in ethanol (100 mL) was prepared. The reaction mixture was heated to reflux for 16 h. Then the reaction mixture cooled to room temperature. The solvent was removed in vacuo and the residue was washed with ether to afford (4-methanesulfonyl-phenyl)-(3-nitro-benzylidene)-amine (10 g, 99%) as a white solid: LC/MS m/e calcd for C14H12N2O4S (M+H)+: 305.33, observed: 305.1.

Workup

  1. customwas prepared
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for 16 h
  4. customThe solvent was removed in vacuo
  5. washthe residue was washed with ether

Sources & evidence

ORD record
ord-5f8571f2b3974ab2ad8308eec4696f73
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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