Triethylamine → Phthalazine

HRID 382928

반응식

HRID 382928 반응식
N=[N+]=[N-].Cl[C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](Cl)=[N:7][N:6]=1.C(N(CC)CC)C>C1(C)C(C)=CC=CC=1>[CH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[N:7][N:6]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 24530Hydrazoic acidHCID 784901,4-Dichlorophthalazine

생성물 1

HCID 9207Phthalazine수율 15.1%

시약·촉매·용매 1

HCID 7237O-Xylene용매

실험 절차

A mixture of the preceding hydrazoic acid (798 mg, 3.91 mmol), 1,4-dichlorophthalazine (778 mg, 3.91 mmol) and triethylamine (0.54 ml, 3.9 mmol) in xylene (28 ml) was heated at reflux under nitrogen for 20.5 h. The mixture was cooled to room temperature, the solvent evaporated in vacuo and the residue partitioned between dichloromethane and water. The aqueous was separated and re-extracted with dichloromethane (×2). The combined extracts were dried (MgSO4), evaporated in vacuo and the residue chromatographed on silica gel eluting with ethyl acetate, then 5% methanol/dichloromethane to afford the title-phthalazine (77 mg, 6%), 1H NMR (360 MHz, CDCl3/d6-DMSO) δ 7.51 (1H, m, Ar—H), 7.55 (1H, s, Ar—H), 7.99 (1H, m, Ar—H), 8.11 (1H, m, Ar—H), 8.24 (1H, m, Ar—H), 8.38 (1H, d, J=7.8 Hz, Ar—H), 8.78 (1H, m, Ar—H), 8.83 (1H, m, Ar—H), 9.18 (1H, br s, Ar—H); MS (ES+) m/e 349 [MH]+.

후처리

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 20.5 h
  3. customthe solvent evaporated in vacuo
  4. customthe residue partitioned between dichloromethane and water
  5. customThe aqueous was separated
  6. extractionre-extracted with dichloromethane (×2)
  7. dry with materialThe combined extracts were dried (MgSO4)
  8. customevaporated in vacuo
  9. customthe residue chromatographed on silica gel eluting with ethyl acetate

출처 및 근거

ORD 기록
ord-e376eff5791544d4bbb7d8163415bc58
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06310203B1

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