4,5-dihydro-4,4-dimethyl-2-(2-thienyl)-oxazole → HCID 70060418、化合物

HRID 1457654ノート

反応式

HRID 1457654 の反応式
C[C:2]1([CH3:12])[CH2:6][O:5][C:4]([C:7]2[S:8][CH:9]=[CH:10][CH:11]=2)=[N:3]1.[CH2:13]([Li])[CH2:14][CH2:15]C.CN1CC(=O)CC2C=CC=C[C:21]=2[O:20]1>O1CCCC1.CCCCCC>[O:20]=[C:21]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:6][C:2]=2[NH:3][C:4](=[O:5])[C:7]2[S:8][CH:9]=[CH:10][C:11]1=2

参加物

6

反応物 3

HCID 50082824,5-dihydro-4,4-dimethyl-2-(2-thienyl)-oxazoleHCID 22099707HCID 22099707、化合物HCID 178418339Butyllithium

生成物 1

HCID 70060418HCID 70060418、化合物

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

反応条件

温度
0 °C

実験手順

To a solution of 9.0 g at 4,5-dihydro-4,4-dimethyl-2-(2-thienyl)oxazole in 200 ml of tetrahydrofuran, cooled to -78° C., is added 20 ml of a 2.5 molar solution of n-butyl lithium in hexane. The mixture is stirred -78° C. for 15 minutes and at 0° C. for 30 minutes. To the stirred solution is added 6.0 g of 2-methylbenzoxazepine-4-one. The mixture is stirred at room temperature for 16 hours quenched with ice cold water and extracted with chloroform. The extract is concentrated to dryness and 100 ml of 40% H2SO4 is added. The mixture is refluxed for 4 hours, cooled to room temperature and filtered to give 9,10-dihydro-4,10-dioxo-4H-thieno [2,3-c][1]benzazepine. The solid is washed with water to give 2.5 g of crystals. The solid is dissolved in 100 ml of dry tetrahydrofuran and 1.0 g of lithium aluminum hydride added. The mixture is refluxed for 16 hours, chilled and ice cold water is added dropwise. The mixture after dilution with water is extracted with chloroform-methanol (3:1) and the extract dried (MgSO4). The solvent is removed and the residue chromatographed over silica gel with ethyl acetate-hexane (1:1) as solvent to give 1.8 g of solid; Mass spectrum (CI) 202 (M+H).

後処理

  1. stirringThe mixture is stirred at room temperature for 16 hours
  2. customquenched with ice cold water
  3. extractionextracted with chloroform
  4. concentrationThe extract is concentrated to dryness and 100 ml of 40% H2SO4
  5. additionis added
  6. temperatureThe mixture is refluxed for 4 hours
  7. temperaturecooled to room temperature
  8. filtrationfiltered

出典と根拠

ORDレコード
ord-6a72ef3945804182a514333c93790111
出典データセット
uspto-grants-1998_12
特許番号
US05849735

反応ノート

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