반응 #88333

반응 방정식

(S)-4-[1-isothiocyanato-2-(4-nitrophenyl)-ethyl]-2-phenylthiazole

acetic hydrazide

→

desired product

수율 93.0%

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

수율 93.0%

용매

EtOH

반응 조건

후처리

1. 1
   기타The solvent is removed under reduced pressure
2. 2
   workup.DISSOLUTIONthe residue is dissolved in POCl3 (3 mL)
3. 3
   온도is heated to 50° C. for 2 hours
4. 4
   기타The solvent is removed in vacuo
5. 5
   workup.DISSOLUTIONthe residue is dissolved in EtOAc (40 mL)
6. 6
   workup.ADDITIONthe resulting solution is treated with 1N NaOH until the pH
7. 7
   추출The solution is extracted with EtOAc
8. 8
   세척The combined aqueous layers are washed with EtOAc
9. 9
   세척washed with brine
10. 10
    건조dried over MgSO4
11. 11
    여과filtered
12. 12
    농축concentrated in vacuo

실험 절차

A solution of (S)-4-[1-isothiocyanato-2-(4-nitrophenyl)-ethyl]-2-phenylthiazole, 53, (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).

출처