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Carbon tetrabromide → 2-[4-(2-bromo-ethoxy)-3-methyl-phenyl]-5,7-dimethoxy-3H-quinazolin-4-one

HRID 591732
ノート
印刷プレビュー

反応式

HRID 591732 の反応式
Br[C:2]([Br:5])(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.OC[CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[NH:44][C:43](=[O:45])[C:42]3[C:37](=[CH:38][C:39]([O:48][CH3:49])=[CH:40][C:41]=3[O:46][CH3:47])[N:36]=2)=[CH:31][C:30]=1[CH3:50]>CN(C=O)C>[Br:5][CH2:2][CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[NH:44][C:43](=[O:45])[C:42]3[C:37](=[CH:38][C:39]([O:48][CH3:49])=[CH:40][C:41]=3[O:46][CH3:47])[N:36]=2)=[CH:31][C:30]=1[CH3:50]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 1360379592-[4-(2-hydroxy-ethoxy)-3-methyl-phenyl]-5,7-dimethoxy-3H-quinazolin-4-one

生成物 1

HCID 1363480552-[4-(2-bromo-ethoxy)-3-methyl-phenyl]-5,7-dimethoxy-3H-quinazolin-4-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

Tetrabromomethane (3.26 g, 9.82 mmol) was added to a solution of triphenylphosphine (2.58 g, 9.82 mmol) in anhydrous DMF (20 mL) at 0° C. A solution of 2-[4-(2-hydroxy-ethoxy)-3-methyl-phenyl]-5,7-dimethoxy-3H-quinazolin-4-one (1.75 g, 4.91 mmol) in DMF (7 mL) was then added dropwise and stirred the reaction mixture at room temperature for 16 hours. The solvent was removed under reduced pressure and the residue was diluted with water (50 mL) and extracted with dichloromethane (4×25 mL). The combined organic phase was washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed and the solid was triturated with ether. The resulting slurry was filtered and washed with ether several times (to remove the triphenylphosphine oxide) and finally with a solution of dichloromethane-ether (1:1) to obtain 2-[4-(2-bromo-ethoxy)-3-methyl-phenyl]-5,7-dimethoxy-3H-quinazolin-4-one as an off-white solid. Yield: 0.70 g (34%).

後処理

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was diluted with water (50 mL)
  3. extractionextracted with dichloromethane (4×25 mL)
  4. washThe combined organic phase was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed
  7. customthe solid was triturated with ether
  8. filtrationThe resulting slurry was filtered
  9. washwashed with ether several times (
  10. customto remove the triphenylphosphine oxide) and finally with a solution of dichloromethane-ether (1:1)

出典と根拠

ORDレコード
ord-477e37b86f15452298b48e4f60896054
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09238640B2

反応ノート

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