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

HRID 25341

반응식

HRID 25341 반응식
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

참가 물질

6

반응물 4

HCID 6420Trichloroacetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 178482577HCID 178482577, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ea6ea98e583549018f8979a87e2c6138
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858640B2

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