2-(Tributylstannyl)-1,3-thiazole → 4,4-Dimethyl-6-(3-thiazol-2-yl-phenyl)1,4-dihydro-benzo[d][1,3]oxazin-2-one

HRID 50722

反応式

HRID 50722 の反応式
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:20]=[CH:19][C:11]3[NH:12][C:13](=[O:18])[O:14][C:15]([CH3:17])([CH3:16])[C:10]=3[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C([Sn](CCCC)(CCCC)[C:26]1[S:27][CH:28]=[CH:29][N:30]=1)CCC>CN(C=O)C>[CH3:16][C:15]1([CH3:17])[O:14][C:13](=[O:18])[NH:12][C:11]2[CH:19]=[CH:20][C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([C:26]4[S:27][CH:28]=[CH:29][N:30]=4)[CH:3]=3)=[CH:9][C:10]1=2

参加物

4

反応物 2

HCID 27632592-(Tributylstannyl)-1,3-thiazoleHCID 98624116-(3-Bromo-phenyl)-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one

生成物 1

HCID 98589994,4-Dimethyl-6-(3-thiazol-2-yl-phenyl)1,4-dihydro-benzo[d][1,3]oxazin-2-one収率 23.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

A mixture of 6-(3-bromo-phenyl)-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one (0.25 g, 0.75 mmol), tri-n-butyl-thiazol-2-yl tin (0.5 g, 1.3 mmol) in DMF (5 mL) was degassed to remove oxygen and then heated under nitrogen at 90° C. for 3 hours. The reaction mixture was cooled to rt and treated with ice-water (70 mL). Ethyl acetate (100 mL) was added and organic layer was separated, washed with brine, and dried (MgSO4). After removal of solvent, the residue was purified by a silica gel column (hexane:ethyl acetate/1:1) to give the title compound as a white solid (60 mg, 23%): mp 223-224° C.; 1H-NMR (DMSO-d6) δ10.4 (s, 1H), 9.13 (s, 1H), 8.45 (s, 1H), 7.94 (bs, 1H), 7.67-7.61 (m, 4H), 7.53 (t, 1H, J=7.68 Hz), 7.00 (d, 1H, J=8.81 Hz), 1.7 (s, 6H); MS (APCI) m/z 337([M+H]+, 100%), Anal. Calc. For C19H16N2O2S.0.25 H2O: C, 66.94; H, 4.88; N, 8.22. Found: C, 66.57; H, 4.65; N, 7.92.

後処理

  1. customwas degassed
  2. customto remove oxygen
  3. temperatureThe reaction mixture was cooled to rt
  4. additiontreated with ice-water (70 mL)
  5. additionEthyl acetate (100 mL) was added
  6. customorganic layer was separated
  7. washwashed with brine
  8. dry with materialdried (MgSO4)
  9. customAfter removal of solvent
  10. customthe residue was purified by a silica gel column (hexane:ethyl acetate/1:1)

出典と根拠

ORDレコード
ord-20ad7ee9eaaf48c1a0c4a1b1893040a6
出典データセット
uspto-grants-2004_03
特許番号
US06713478B2

関連ノート

読み込み中…