HCID 57680507, compound → HCID 57680503, compound

HRID 600214Notes

Reaction equation

HRID 600214 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][S:12][C:11](=[O:14])[N:10]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-])=O)[CH:17]=3)[N:9]=2)=[CH:4][CH:3]=1.[H][H]>C1COCC1.[Ni]>[NH2:22][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][CH:19]=1)[CH2:15][N:10]1[N:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH2:13][S:12][C:11]1=[O:14]

Participants

5

Reactant 2

HCID 57680507HCID 57680507, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57680503HCID 57680503, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

5.47 g of 5-(4-chlorophenyl)-3-(3-nitrobenzyl)-3,6-dihydro-1,3,4-thiadiazin-2-one is dissolved in 100 ml of THF, and 1.3 g of Raney nickel is subsequently added. Hydrogen is subsequently passed in until starting material is no longer detectable. For work-up, the catalyst is filtered off, washed with THF, and the filtrate is evaporated to dryness and recrystallised from dichloromethane/diethyl ether, giving 4.6 g (94%) of 3-(3-aminobenzyl)-5-(4-chlorophenyl)-3,6-dihydro-1,3,4-thiadiazin-2-one.

Workup

  1. filtrationFor work-up, the catalyst is filtered off
  2. washwashed with THF
  3. customthe filtrate is evaporated to dryness
  4. customrecrystallised from dichloromethane/diethyl ether

Sources & evidence

ORD record
ord-359a52ab4a5d4e3096bd5d8a0ea139f0
Source dataset
uspto-grants-2011_03
Patent number
US07902186B2

Reaction notes

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