3-(4-Nitrobenzyl)-5-(3,4-dimethoxyphenyl)-6-ethyl-3,6-dihydro-1,3,4-thiadiazin-2-one → 3-(4-Aminobenzyl)-5-(3,4-dimethoxyphenyl)-6-ethyl-3,6-dihydro-1,3,4-thiadiazin-2-one

HRID 377166Notes

Reaction equation

HRID 377166 reaction equation
[N+:1]([C:4]1[CH:29]=[CH:28][C:7]([CH2:8][N:9]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=3)[CH:12]([CH2:25][CH3:26])[S:11][C:10]2=[O:27])=[CH:6][CH:5]=1)([O-])=O>O1CCCC1.[Ni]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=3)[CH:12]([CH2:25][CH3:26])[S:11][C:10]2=[O:27])=[CH:28][CH:29]=1

Participants

4

Reactant 1

HCID 98019423-(4-Nitrobenzyl)-5-(3,4-dimethoxyphenyl)-6-ethyl-3,6-dihydro-1,3,4-thiadiazin-2-one

Product 1

HCID 101346893-(4-Aminobenzyl)-5-(3,4-dimethoxyphenyl)-6-ethyl-3,6-dihydro-1,3,4-thiadiazin-2-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3.9 g of 3-(4-nitrobenzyl)-5-(3,4-dimethoxyphenyl)-6-ethyl-3,6-dihydro-1,3,4-thiadiazin-2-one in 40 ml of tetrahydrofuran is hydrogenated in the presence of Raney nickel. The catalyst is filtered off and the solution is concentrated. Recrystallization gives 3-(4-aminobenzyl)-5-(3,4-dimethoxyphenyl)-6-ethyl-3,6-dihydro-1,3,4-thiadiazin-2-one, m.p. 105°.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe solution is concentrated
  3. customRecrystallization

Sources & evidence

ORD record
ord-c3110df07a8348efb077c5629e6babd6
Source dataset
uspto-grants-2000_02
Patent number
US06025354

Reaction notes

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