Hydrogen Sulfide → 2,4-dihydro-5-phenyl-2-[1-(9H-fluoren-9-ylmethoxycarbonyl)-4-piperidinyl]-3H-1,2,4-triazol-3-one

HRID 1782686Notes

Reaction equation

HRID 1782686 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[CH2:23][CH2:22][CH:21]([NH:24][NH2:25])[CH2:20][CH2:19]3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.S.O1[CH2:31][CH2:30][CH2:29][CH2:28]1>>[C:29]1([C:28]2[NH:18][C:16](=[O:15])[N:24]([CH:21]3[CH2:22][CH2:23][N:18]([C:16]([O:15][CH2:14][CH:12]4[C:13]5[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=5[C:6]5[C:11]4=[CH:10][CH:9]=[CH:8][CH:7]=5)=[O:17])[CH2:19][CH2:20]3)[N:25]=2)[CH:30]=[CH:31][CH:13]=[CH:1][CH:2]=1

Participants

4

Reactant 3

HCID 402Hydrogen SulfideHCID 8028Tetrahydrofuran2×HCID 18321149(9H-fluoren-9-yl)methyl 4-hydrazinylpiperidine-1-carboxylate

Product 1

HCID 1356275992,4-dihydro-5-phenyl-2-[1-(9H-fluoren-9-ylmethoxycarbonyl)-4-piperidinyl]-3H-1,2,4-triazol-3-one

Procedure

The solutions of 5.56 g (0.0165 mol) of [1-(9H-fluoren-9-ylmethoxycarbonyl)-4-piperidinyl]-hydrazine in 60 ml of tetrahydrofuran and 3.7 g (0.0177 mol) of N-(ethoxycarbonyl)-benzothionamide in 30 ml of tetrahydrofuran were combined and refluxed for 1 hour, whereupon hydrogen sulphide was released. The solvent was distilled off in vacuo, the oily residue remaining was boiled with a little acetonitrile. The mixture was allowed to cool, then additionally cooled from outside with ice water and the resulting precipitate was suction filtered. 4.0 g (52% of theory) of colourless crystals were obtained, melting point 142° C. and Rf=0.38 (eluant 4).

Workup

  1. distillationThe solvent was distilled off in vacuo
  2. temperatureto cool
  3. temperatureadditionally cooled from outside with ice water
  4. filtrationfiltered
  5. custom4.0 g (52% of theory) of colourless crystals were obtained

Sources & evidence

ORD record
ord-fcb9f893e85643fa826eef35bcb0e1ab
Source dataset
uspto-grants-2009_03
Patent number
US07498325B2

Reaction notes

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