HCID 13427187, compound → HCID 13427193, compound

HRID 2372371Notes

Reaction equation

HRID 2372371 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[N:12][S:13][C:14]=2[C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)=[CH:6][CH:5]=1)([O-])=O>CCO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:11]=[N:12][S:13][C:14]=2[C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 13427187HCID 13427187, compound

Product 1

HCID 13427193HCID 13427193, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Thiadiazole 36 (11.8 g, 36.1 mmol) in EtOH (200 ml) was hydrogenated over 5% Pd/C (3.6 g) at 50 psi for 16 hours. The solution was filtered through a celite pad and washed with EtOH. The solvent was removed under reduced pressure, and the crude solid was recrystallized from EtOAc/MeOH to afford 32 (9.2 g, 95.1%), m.p. 236° C. (decomposes).

Workup

  1. filtrationThe solution was filtered through a celite pad
  2. washwashed with EtOH
  3. customThe solvent was removed under reduced pressure
  4. customthe crude solid was recrystallized from EtOAc/MeOH

Sources & evidence

ORD record
ord-4f27aa6c3b50430d9d2e3367cd145d69
Source dataset
uspto-grants-1992_03
Patent number
US05098918

Reaction notes

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