HCID 59372566, compound → HCID 67428865, compound

HRID 1966417Notes

Reaction equation

HRID 1966417 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][CH:17]=1)[CH2:7][NH:8][S:9]([NH:12][CH2:13][CH3:14])(=[O:11])=[O:10])([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][CH:17]=1)[CH2:7][NH:8][S:9]([NH:12][CH2:13][CH3:14])(=[O:11])=[O:10]

Participants

4

Reactant 1

HCID 59372566HCID 59372566, compound

Product 1

HCID 67428865HCID 67428865, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N-(3-nitrobenzyl)-N′-ethylsulfamide was dissolved in methanol (100 mL) and to the solution was added 10% Pd—C. The reaction mixture was reacted under hydrogen atmosphere (˜40 psi) for 1 h. The catalyst was filtered off over celite and washed with methanol. The filtrate was evaporated to give N-(3-aminobenzyl)-N′-ethylsulfamide. 1H NMR (DMSO-d6): δ 1.03 (t, J=7.2 Hz, 3H), 2.83 (p, J=6.9 Hz, 2H), 3.81 (d, J=6.3 Hz, 2H), 5.02 (s, 2H), 6.41 (t, J=7.8 Hz, 2H), 6.51 (s, 1H), 6.76 (t, J=5.7 Hz, 1H), 6.91 (t, J=7.5 Hz, 1H), 7.16 (t, J=6.3 Hz, 1H).

Workup

  1. customThe reaction mixture was reacted under hydrogen atmosphere (˜40 psi) for 1 h
  2. filtrationThe catalyst was filtered off over celite
  3. washwashed with methanol
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-962e60a2828045feb4eeb772e19c8d48
Source dataset
uspto-grants-2013_04
Patent number
US08420659B2

Reaction notes

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