Dimethyl Disulfide → Dimethyl-(5-methylsulfanyl-2-triisopropylsilanyl-2,7,8,9-tetrahydro-6-oxa-2-azabenzo[cd]-azulen-8-yl)amine

HRID 25338

反応式

HRID 25338 の反応式
Br[C:2]1[O:11][CH2:10][C:9]2[CH:8]([N:12]([CH3:14])[CH3:13])[CH2:7][C:6]3=[CH:15][N:16]([Si:18]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20])[CH:17]=[C:4]([C:5]=23)[CH:3]=1.[Li]CCCC.[CH3:33][S:34]SC>O1CCCC1.[Cl-].[NH4+]>[CH3:14][N:12]([CH3:13])[CH:8]1[C:9]2[CH2:10][O:11][C:2]([S:34][CH3:33])=[CH:3][C:4]3=[CH:17][N:16]([Si:18]([CH:22]([CH3:24])[CH3:23])([CH:25]([CH3:27])[CH3:26])[CH:19]([CH3:20])[CH3:21])[CH:15]=[C:6]([C:5]=23)[CH2:7]1

参加物

6

反応物 3

HCID 12232Dimethyl DisulfideHCID 69736345(5-Bromo-2-triisopropylsilanyl-2,7,8,9-tetrahydro-6-oxa-2-azabenzo[cd]azulen-8-yl)dimethylamineHCID 178418339Butyllithium

生成物 1

HCID 69736433Dimethyl-(5-methylsulfanyl-2-triisopropylsilanyl-2,7,8,9-tetrahydro-6-oxa-2-azabenzo[cd]-azulen-8-yl)amine収率 69%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 25517Ammonium Chloride溶媒

実験手順

A solution of compound (42) 451 mg in dry tetrahydrofuran 5 ml was cooled at −70° C. n-BuLi (1.56 mol/l hexane solution) 1.3 ml was added dropwise to the solution and the mixture was stirred for 1 h. Then, dimethyldisulfide 185 μl was added and the mixture was stirred for 2 h. The reaction mixtures was diluted with an aqueous ammonium chloride solution and extracted with ethyl acetate. 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 ethyl acetate:hexane (1:5) to give the titled compound as colorless crystals, 289.8 mg. Yield 69%. This was recrystallized from hexane to give the titled compound as colorless crystals, m.p. 77-79° C.

後処理

  1. additionwas added dropwise to the solution
  2. stirringthe mixture was stirred for 2 h
  3. customThe reaction mixtures
  4. extractionextracted with ethyl acetate
  5. washThe extracts were washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue obtained
  9. customwas chromatographed on aluminum oxide in ethyl acetate:hexane (1:5)

出典と根拠

ORDレコード
ord-88856aa7067d48b783d67b38e16f531d
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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