HCID 4788657, compound → HCID 19813881, compound

HRID 467333Notes

Reaction equation

HRID 467333 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6](=[O:18])[C:7]1[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[C:9]([N+:15]([O-])=O)[CH:8]=1.[H][H]>[Pd].C(OCC)(=O)C>[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6](=[O:18])[C:7]1[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[C:9]([NH2:15])[CH:8]=1

Participants

5

Reactant 2

HCID 4788657HCID 4788657, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19813881HCID 19813881, compoundYield 94.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of N-(2-methoxyethyl)-4-methylthio-3-nitrobenzamide (1.6 g) and palladium on charcoal (1.1 g; 5%) in ethyl acetate (60 ml) was shaken under an atmosphere of hydrogen at atmospheric pressure until hydrogen uptake ceased. The mixture was filtered and the residue was rinsed with ethyl acetate. The filtrate was concentrated in vacuo to leave N-(2-methoxyethyl)-4-methylthio-3-aminobenzamide (1.35 g) in the form of an oil that crystallised on standing, m.p. 66°-68° C. [Elemental analysis: C,54.8; H,6.69; N,11.5; S,12.9%; calculated: C,54.98; H,6.71; N,11.66; S,13.34%].

Workup

  1. filtrationThe mixture was filtered
  2. washthe residue was rinsed with ethyl acetate
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e089200dbe63409fb8a2873b208092ed
Source dataset
uspto-grants-1992_10
Patent number
US05159114

Reaction notes

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