Acetohydrazide → (S)-5-methyl-N-(2-(4-nitrophenyl)-1-(2-phenylthiazol-4-yl)ethyl)-1,3,4-thiadiazol-2-amine

HRID 1714532Notes

Reaction equation

HRID 1714532 reaction equation
[N:1]([C@H:4]([C:15]1[N:16]=[C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[S:18][CH:19]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)=[C:2]=[S:3].[C:26]([NH:29][NH2:30])(=O)[CH3:27]>CCO>[CH3:27][C:26]1[S:3][C:2]([NH:1][C@H:4]([C:15]2[N:16]=[C:17]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[S:18][CH:19]=2)[CH2:5][C:6]2[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=2)=[N:30][N:29]=1

Participants

4

Reactant 2

HCID 14039AcetohydrazideHCID 57841130(S)-2-phenyl-4-(1-isothiocyanato-2-(4-nitrophenyl)ethyl)thiazole

Product 1

HCID 57841129(S)-5-methyl-N-(2-(4-nitrophenyl)-1-(2-phenylthiazol-4-yl)ethyl)-1,3,4-thiadiazol-2-amineYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (S)-4-[1-isothiocyanato-2-(4-nitrophenyl)-ethyl]-2-phenylthiazole, 39, (332 mg, 0.876 mmol) and acetic hydrazide (65 mg, 0.876 mmol) in EtOH (5 mL) is refluxed for 2 hours. The solvent is removed under reduced pressure, the residue is dissolved in POCl3 (3 mL) and the resulting solution is stirred at room temperature for 18 hours after which the solution is heated to 50° C. for 2 hours. The solvent is removed in vacuo and the residue is dissolved in EtOAc (40 mL) and the resulting solution is treated with 1N NaOH until the pH remains approximately 8. The solution is extracted with EtOAc. The combined aqueous layers are washed with EtOAc, the organic layers combined, washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to afford 0.345 g (93% yield) of the desired product as a yellow solid. 1H NMR (CDCl3) 8.09 (d, J=8.4 Hz, 2H), 7.91 (m, 2H), 7.46 (m, 4H), 7.44 (s, 1H), 5.23 (m, 1H), 3.59 (m, 2H), 2.49 (s, 3H). ESI+ MS 424 (M+1).

Workup

  1. customThe solvent is removed under reduced pressure
  2. dissolutionthe residue is dissolved in POCl3 (3 mL)
  3. temperatureis heated to 50° C. for 2 hours
  4. customThe solvent is removed in vacuo
  5. dissolutionthe residue is dissolved in EtOAc (40 mL)
  6. additionthe resulting solution is treated with 1N NaOH until the pH
  7. extractionThe solution is extracted with EtOAc
  8. washThe combined aqueous layers are washed with EtOAc
  9. washwashed with brine
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cd02276d78ff4586b6d542b0cd2e7af5
Source dataset
uspto-grants-2010_09
Patent number
US07795444B2

Reaction notes

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