Trichloroacetyl chloride → 8-Dimethylamino-2,7,8,9-tetrahydro-6-oxa-2-azabenzo[cd]-azulene-5-carbonitrile

HRID 25341

反応式

HRID 25341 の反応式
C(N(CC)CC)C.ClC(Cl)(Cl)C(Cl)=O.[CH3:15][N:16]([CH3:33])[CH:17]1[C:26]2[CH2:25][O:24][C:23]([CH:27]=[N:28]O)=[CH:22][C:21]3=[CH:30][NH:31][CH:32]=[C:19]([C:20]=23)[CH2:18]1.C(=O)([O-])O.[Na+]>ClCCl>[CH3:15][N:16]([CH3:33])[CH:17]1[C:26]2[CH2:25][O:24][C:23]([C:27]#[N:28])=[CH:22][C:21]3=[CH:30][NH:31][CH:32]=[C:19]([C:20]=23)[CH2:18]1

参加物

6

反応物 4

HCID 6420Trichloroacetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 178482577HCID 178482577、化合物

生成物 1

HCID 697371988-Dimethylamino-2,7,8,9-tetrahydro-6-oxa-2-azabenzo[cd]-azulene-5-carbonitrile収率 98%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Triethylamine 33 μl and trichloroacetyl chloride 13 μl were added to a solution of compound (47) 28.9 mg in dichloromethane 2 ml with cooling ice and the mixture was stirred with cooling in ice and at room temperature for 18 h. A saturated sodium hydrogencarbonate solution was added thereto for alkalinization. The mixture was extracted with chloroform. The extracts were washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue obtained was chromatographed on aluminum oxide in chloroform:methanol (97:3) to give the titled compound 26.3 mg as colorless crystals. Yield 98%. Furthermore, the titled compound was recrystallized from methanol-isopropyl ether to give colorless crystals, m.p. 205-207° C.

後処理

  1. extractionThe mixture was extracted with chloroform
  2. washThe extracts were washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue obtained
  6. customwas chromatographed on aluminum oxide in chloroform:methanol (97:3)

出典と根拠

ORDレコード
ord-ea6ea98e583549018f8979a87e2c6138
出典データセット
uspto-grants-2005_02
特許番号
US06858640B2

関連ノート

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