Methane → 4-(4-Aminobenzyl)thiomorpholine 1,1-dioxide

HRID 2236518Notes

Reaction equation

HRID 2236518 reaction equation
[N+:1]([C:4]1[CH:18]=[CH:17][C:7]([CH2:8][N:9]2[CH2:14][CH2:13][S:12](=[O:16])(=[O:15])[CH2:11][CH2:10]2)=[CH:6][CH:5]=1)([O-])=O.C.O.NN>CO>[NH2:1][C:4]1[CH:18]=[CH:17][C:7]([CH2:8][N:9]2[CH2:10][CH2:11][S:12](=[O:16])(=[O:15])[CH2:13][CH2:14]2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 297MethaneHCID 24654Hydrazine hydrate (1:1)HCID 225697624-(4-Nitro-benzyl)-thiomorpholine 1,1-dioxide

Product 1

HCID 27796824-(4-Aminobenzyl)thiomorpholine 1,1-dioxide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(4-Nitro-benzyl)-thiomorpholine 1,1-dioxide (110 mg, 0.41 mmol) is dissolved in MeOH (7 mL). To this solution is added FeCl3.6H2O (−20 mg, 0.07 mmol) and active Charcoal (12 mg, 1.0 mmol). The suspension is heated to reflux. Hydrazine hydrate (0.5 mL) is added, and reflux is continued for 4 h until full conversion, the active Charcoal is filtered off through Celite, and the MeOH is removed under reduced pressure. The residue (85 mg, 86%) is directly used in the next step.

Workup

  1. temperatureThe suspension is heated to reflux
  2. temperaturereflux
  3. filtrationthe active Charcoal is filtered off through Celite
  4. customthe MeOH is removed under reduced pressure

Sources & evidence

ORD record
ord-3a1889ccfea64160880d9972ed412d29
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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