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Water → 3,6-Dichloro-4-pyrrolidin-1-ylpyridazine

HRID 1369428
ノート
印刷プレビュー

反応式

HRID 1369428 の反応式
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[C:7]1[CH:12]=[C:11]([Cl:13])[N:10]=[N:9][C:8]=1[Cl:14].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Cl:14][C:8]1[N:9]=[N:10][C:11]([Cl:13])=[CH:12][C:7]=1[N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 220306484-Bromo-3,6-dichloropyridazine

生成物 1

HCID 124492983,6-Dichloro-4-pyrrolidin-1-ylpyridazine収率 92%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Pyrrolidine (3.36 ml, 40 mmol) was added to a stirred solution/suspension of 4-bromo-3,6-dichloropyridazine (8.3 g, 36 mmol) and potassium carbonate (13.8 g, 0.1 mol) in dry DMF (100 ml) at room temperature under nitrogen. The mixture was stirred at room temperature for 16 hours, then at 60° C. for 3 hours. The reaction was poured into water (250 ml). The aqueous was extracted with ethyl acetate (×3). The combined extracts were dried (MgSO4), filtered and evaporated. The residue was purified by chromatography on silica gel, eluting with 0.5% methanol/dichloromethane to afford the title pyridazine (7.2 g, 92%) as a colourless oil. 1H NMR (250 MHz, CDCl3) 2.00-2.05 (4H, m) 3.61-3.69 (4H, m), 6.46 (1H, s). MS (ES+) 218 [MH]+, 220 [MH]+.

後処理

  1. waitat 60° C. for 3 hours
  2. extractionThe aqueous was extracted with ethyl acetate (×3)
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by chromatography on silica gel
  7. washeluting with 0.5% methanol/dichloromethane

出典と根拠

ORDレコード
ord-2427b3de623d47b6baf07f5842d16163
出典データセット
uspto-grants-2003_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06579875B1

反応ノート

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