5-(4-amino-3-nitrophenyl)-6-methyl-3,6-dihydro-2H-1,3,4-thiadiazin-2-one → HCID 59569007, compound

HRID 1517195Notes

Reaction equation

HRID 1517195 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]([CH3:14])[S:12][C:11](=[O:15])[NH:10][N:9]=2)=[CH:4][C:3]=1[N+:16]([O-])=O>[Ni].CO>[NH2:16][C:3]1[CH:4]=[C:5]([C:8]2[CH:13]([CH3:14])[S:12][C:11](=[O:15])[NH:10][N:9]=2)[CH:6]=[CH:7][C:2]=1[NH2:1]

Participants

4

Reactant 1

HCID 595690255-(4-amino-3-nitrophenyl)-6-methyl-3,6-dihydro-2H-1,3,4-thiadiazin-2-one

Product 1

HCID 59569007HCID 59569007, compoundYield 86.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

13.7 g (51.4 mM) of 5-(4-amino-3-nitrophenyl)-6-methyl-3,6-dihydro-2H-1,3,4-thiadiazin-2-one are placed under a hydrogen atmosphere at 3 bar for 4 hours in the presence of 24 g of Raney nickel in 280 ml of methanol. The reaction medium is then filtered and the filtrate is concentrated under vacuum to give 10.5 g of 5-(3,4-diaminophenyl)-6-methyl-3,6-dihydro-2H-1,3,4-thiadiazin-2-one in the form of a solid, which is treated with diisopropyl ether, filtered off and stored under argon at low temperature.

Workup

  1. filtrationThe reaction medium is then filtered
  2. concentrationthe filtrate is concentrated under vacuum

Sources & evidence

ORD record
ord-e06493097c134245a126c749599f588a
Source dataset
uspto-grants-2012_07
Patent number
US08232272B2

Reaction notes

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