Isatoic Anhydride → 2-amino-N'-(4-chlorophenyl)benzohydrazide

HRID 30402

反応式

HRID 30402 の反応式
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.C(N(C(C)C)CC)(C)C.[C:20]12[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=1)[NH:25]C(=O)O[C:21]2=[O:22]>CCO>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH:10][C:21](=[O:22])[C:20]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[NH2:25])=[CH:5][CH:4]=1

参加物

5

反応物 3

HCID 8359Isatoic AnhydrideHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 81531Diisopropylethylamine

生成物 1

HCID 218205992-amino-N'-(4-chlorophenyl)benzohydrazide収率 50%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

4-Chlorophenylhydrazine hydrochloride (2.105 g, 14.76 mmol) was suspended in EtOH (25 ml), treated with di-isopropylethylamine (2.253 ml, 12.93 mmol) and stirred for 30 minutes. Isatoic anhydride (1.918 g, 11.76 mmol) was added and the mixture was heated to reflux for 3 hours. The reaction mixture was cooled to room temperature and stirred overnight. The material was concentrated to dryness and the resulting residue was partitioned between EtOAc (˜25 ml) and 50% saturated NaCl (3×30 ml). The organic layer (also containing a small amount of emulsion which would not dissipate over 3 extractions) was dried over MgSO4 and concentrated to an orange solid. The material was triturated with EtOAc, filtered and rinsed with additional EtOAc. The filtrate was concentrated to dryness and treated with DCM (dichloromethane). The mixture was stirred overnight. The mixture was filtered, rinsed with DCM and the solid dried to provide 1.538 g (50%) of 2-amino-benzoic acid N′-(4-chloro-phenyl)-hydrazide (Intermediate 40) as a mauve-colored solid. MS (APCI): (M+1)=262.1, (M−1)=260.0.

後処理

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 hours
  3. stirringstirred overnight
  4. concentrationThe material was concentrated to dryness
  5. customthe resulting residue was partitioned between EtOAc (˜25 ml) and 50% saturated NaCl (3×30 ml)
  6. additionThe organic layer (also containing a small amount of emulsion which would not
  7. extractiondissipate over 3 extractions)
  8. dry with materialwas dried over MgSO4
  9. concentrationconcentrated to an orange solid
  10. customThe material was triturated with EtOAc
  11. filtrationfiltered
  12. washrinsed with additional EtOAc
  13. concentrationThe filtrate was concentrated to dryness
  14. additiontreated with DCM (dichloromethane)
  15. stirringThe mixture was stirred overnight
  16. filtrationThe mixture was filtered
  17. washrinsed with DCM
  18. customthe solid dried

出典と根拠

ORDレコード
ord-fafd3337a3cd457db53e4e5251973741
出典データセット
uspto-grants-2008_09
特許番号
US07423054B2

関連ノート

読み込み中…