Ethyl Acetate → 1-Phenethyl-3-[3-(4-pyridyl)propyl]-2-imidazolidinethione

HRID 11469

反応式

HRID 11469 の反応式
O[CH2:2][CH2:3][N:4]([CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:5]([NH:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1)=[S:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.C(OCC)(=O)C>O1CCCC1>[CH2:17]([N:4]1[CH2:3][CH2:2][N:7]([CH2:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[C:5]1=[S:6])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 219739881-(2-Hydroxyethyl)-1-phenethyl-3-[3-(4-pyridyl)propyl]thiourea

生成物 1

HCID 219742041-Phenethyl-3-[3-(4-pyridyl)propyl]-2-imidazolidinethione収率 19%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Anhydrous tetrahydrofuran (2.5 ml) was added to a mixture of 1-(2-hydroxyethyl)-1-phenethyl-3-[3-(4-pyridyl)propyl]thiourea (Compound No. 7-2) (601 mg, 1.75 mmol) and triphenylphosphine (913 mg, 3.49 mmol), and the whole was stirred under ice/methanol-cooling. A solution of diisopropyl azodicarboxylate (710 mg, 3.49 mmol) in anhydrous tetrahydrofuran was added dropwise thereto, and after 10 minutes, ethyl acetate (100 ml) was added to the reaction mixture. The whole was washed with a saturated aqueous sodium bydrogencarbonate solution (40 ml) and saturated brine (40 ml) successively, and the organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography, and the obtained solid was filtered off with hexane to give 107 mg (19%) of the titled compound as crystals.

後処理

  1. temperaturecooling
  2. washThe whole was washed with a saturated aqueous sodium bydrogencarbonate solution (40 ml) and saturated brine (40 ml) successively
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography
  6. filtrationthe obtained solid was filtered off with hexane

出典と根拠

ORDレコード
ord-af7cd9850f9147579b0f06543321c27a
出典データセット
uspto-grants-2006_08
特許番号
US07098226B2

関連ノート

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