Triethylamine → Phthalazine

HRID 382928

反応式

HRID 382928 の反応式
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

参加物

5

反応物 3

HCID 8471TriethylamineHCID 24530Hydrazoic acidHCID 784901,4-Dichlorophthalazine

生成物 1

HCID 9207Phthalazine収率 15.1%

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-e376eff5791544d4bbb7d8163415bc58
出典データセット
uspto-grants-2001_10
特許番号
US06310203B1

関連ノート

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