3,5-Dichloro-4-(4'-methoxy-3'-(6-methoxy-3-pyridylmethyl)phenylthio)-nitrobenzene → 3,5-Dichloro-4-(4'-methoxy-3'-(6-methoxy-3-pyridylmethyl)phenylthio) aniline

HRID 35288Notes

Reaction equation

HRID 35288 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:27]([O-])=O)[CH:5]=[C:6]([Cl:26])[C:7]=1[S:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([CH2:17][C:18]2[CH:19]=[N:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=2)[CH:10]=1>C(O)(=O)C.[Fe]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([Cl:26])[C:7]=1[S:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([CH2:17][C:18]2[CH:19]=[N:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=2)[CH:10]=1)[NH2:27]

Participants

4

Reactant 1

HCID 146735383,5-Dichloro-4-(4'-methoxy-3'-(6-methoxy-3-pyridylmethyl)phenylthio)-nitrobenzene

Product 1

HCID 146735393,5-Dichloro-4-(4'-methoxy-3'-(6-methoxy-3-pyridylmethyl)phenylthio) aniline

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

3,5-Dichloro-4-(4'-methoxy-3'-(6-methoxy-3-pyridylmethyl)phenylthio)-nitrobenzene (28.60 g) and iron powder (35 g) were stirred with heating in glacial acetic acid (250 ml) at 90° for 40 minutes. The mixture was cooled, filtered, then evaporated to dryness and the resulting gum redissolved in chloroform, washed with water (twice), dried over anhydrous magnesium sulphate and evaporated to give the crude product as a light brown gum (27.17 g). This gum was chromatographed on silica gel using ethyl acetate-petroleum spirit (60°-80°, gradient elution) as eluant. 3,5-Dichloro-4-(4'-methoxy-3'-(6-methoxy-3-pyridylmethyl)phenylthio) aniline was isolated as a pale yellow solid (21.29 g, 79%), m.p. 114°-115°.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. customevaporated to dryness
  4. dissolutionthe resulting gum redissolved in chloroform
  5. washwashed with water (twice),
  6. dry with materialdried over anhydrous magnesium sulphate
  7. customevaporated
  8. customto give the crude product as a light brown gum (27.17 g)
  9. customThis gum was chromatographed on silica gel
  10. customethyl acetate-petroleum spirit (60°-80°, gradient elution)

Sources & evidence

ORD record
ord-258208a458734b6d80c27d9475f8caa2
Source dataset
uspto-grants-1988_08
Patent number
US04766121

Reaction notes

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