Chlorosuccinimide → 5-Chloro-6-[3-(trifluoromethyl)phenyl]-4-pyridazinamine

HRID 52775ノート

反応式

HRID 52775 の反応式
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([C:9]2[N:14]=[N:13][CH:12]=[C:11]([NH2:15])[CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[Cl:18]N1C(=O)CCC1=O.CCOC(C)=O.C1CCCCC1>CC#N>[Cl:18][C:10]1[C:11]([NH2:15])=[CH:12][N:13]=[N:14][C:9]=1[C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:16])[F:17])[CH:4]=1

参加物

5

反応物 3

HCID 31398ChlorosuccinimideHCID 199596756-[3-(Trifluoromethyl)phenyl]-4-pyridazinamineHCID 21867204Cyclohexane ethylacetate

生成物 1

HCID 199596635-Chloro-6-[3-(trifluoromethyl)phenyl]-4-pyridazinamine収率 52.1%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

6-[3-(Trifluoromethyl)phenyl]-4-pyridazinamine (2.0 g, 0.0084 mole, Compound No. 4) and N-chlorosuccinimide (0.61 g, 0.004 mole) were refluxed under N2 in CH3CN (50 mL) for 1.5 h. After this time no starting material was present by TLC. The mixture was partitioned between EtOAc/water. The organic layer was extracted again with water, dried (MgSO4), filtered and evaporated to give a crude oil. The oil was chromatographed on a Prep-500 using EtOAc/cyclohexane (9:1) to give a crude solid. The solid was recrystal-lized from EtOAc/cyclohexane to give 5-chloro-6-[3-(trifluoromethyl)phenyl]-4-pyridazinamine (0.57 g, 50% yield, Compound No. 35) as a tan solid.

後処理

  1. customThe mixture was partitioned between EtOAc/water
  2. extractionThe organic layer was extracted again with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customto give a crude oil
  7. customThe oil was chromatographed on a Prep-500 using EtOAc/cyclohexane (9:1)
  8. customto give a crude solid

出典と根拠

ORDレコード
ord-d052b4381e5c4c09a46e158086914306
出典データセット
uspto-grants-1997_04
特許番号
US05616789

反応ノート

読み込み中…