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

HRID 60055

反応式

HRID 60055 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1d43c19c4ace4ebfbbf52d5261641189
出典データセット
uspto-grants-2016_09
特許番号
US09440963B2

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