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

HRID 30402

반응식

HRID 30402 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fafd3337a3cd457db53e4e5251973741
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423054B2

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