Ammonium Chloride → 4,6-Diphenyl-4,5-dihydropyridazin-3(2h)-one

HRID 383552

反応式

HRID 383552 の反応式
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9]1([C:15]2[CH:16]=[CH:17][C:18](=[O:21])[NH:19][N:20]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Cl-].[NH4+]>C1COCC1.C1(C)C=CC=CC=1>[C:9]1([C:15]2[CH2:16][CH:17]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:18](=[O:21])[NH:19][N:20]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

参加物

6

反応物 3

HCID 25517Ammonium ChlorideHCID 751063-Phenyl-6-pyridazoneHCID 178418255HCID 178418255、化合物

生成物 1

HCID 2839154,6-Diphenyl-4,5-dihydropyridazin-3(2h)-one収率 50%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

135 ml (135 mmole) of a solution of phenylmagnesium bromide (1M) in THF was added to a hot suspension of 6-phenylpyridazinone compound 7.8 g (45 mmole) in dry toluene (50 ml). The mixture was refluxed for 8 h, left overnight at ambient temperature, then decomposed with a saturated solution of ammonium chloride. The organic layer was separated, and the aqueous layer was extracted with 100 ml of ethyl acetate. The solvent was removed and the residue was crystallized from ethanol. The crystals were collected by filtering and dried over a medium frit sintered glass funnel in vacuo to give 5.6 g of white crystals. Yield was 50%, confirmed by ESI-MS. ESI-MS: m/z 250.1 (M+H+).

後処理

  1. temperatureThe mixture was refluxed for 8 h
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with 100 ml of ethyl acetate
  4. customThe solvent was removed
  5. customthe residue was crystallized from ethanol
  6. customThe crystals were collected
  7. filtrationby filtering
  8. customdried over a medium frit sintered glass funnel in vacuo

出典と根拠

ORDレコード
ord-003b66cc259545ada346cd79dbbda287
出典データセット
uspto-grants-2013_02
特許番号
US08367672B2

関連ノート

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