Sodium ethoxide → 5-Methyl-2,4-bis(4-bromophenyl)pyrimidine

HRID 2293115ノート

反応式

HRID 2293115 の反応式
[O-][CH2:2]C.[Na+].[Na].C1(S(O)(=O)=O)C=CC=CC=1.[Br:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([NH2:23])=[NH:22])=[CH:19][CH:18]=1.CN(C)C=[C:29](C)[C:30]([C:32](=O)[C:33]1[CH:38]=[CH:37][C:36]([Br:39])=[CH:35][CH:34]=1)=O>C(O)C>[CH3:2][C:30]1[C:32]([C:33]2[CH:34]=[CH:35][C:36]([Br:39])=[CH:37][CH:38]=2)=[N:22][C:21]([C:20]2[CH:24]=[CH:25][C:17]([Br:16])=[CH:18][CH:19]=2)=[N:23][CH:29]=1

参加物

6

反応物 4

HCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 21476408p-Bromobenzamidine benzenesulfonateHCID 54209384HCID 54209384、化合物

生成物 1

HCID 107161785-Methyl-2,4-bis(4-bromophenyl)pyrimidine

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

Sodium ethoxide (0.06 mole), (prepared from 1.38 g sodium in 75 mL absolute ethanol) is gradually added to a stirred suspension of p-bromobenzamidine benzenesulfonate (10.7 g, 0.03 mole), and 3-dimethylamino-1-(4-bromobenzoyl)-2-methylpropen-1-one (8.04 g, 0.03 mole) in 75 mL absolute ethanol, and the reaction mixture is heated under reflux for 12-16 hr (TLC monitored). Solvent is distilled and the residue is treated with 150 mL water. The resulting solid is filtered, washed with water and dried. The product is dissolved in 250 mL chloroform, dried over anhydrous sodium sulfate, filtered, concentrated and recrystallized from chloroform:ether (1:4) to yield 7.75 g (64%) of a white crystallized solid, mp 136°-137° C.

後処理

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 12-16 hr (TLC monitored)
  3. distillationSolvent is distilled
  4. additionthe residue is treated with 150 mL water
  5. filtrationThe resulting solid is filtered
  6. washwashed with water
  7. customdried
  8. dissolutionThe product is dissolved in 250 mL chloroform
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customrecrystallized from chloroform:ether (1:4)
  13. customto yield 7.75 g (64%) of
  14. customa white crystallized solid, mp 136°-137° C.

出典と根拠

ORDレコード
ord-23aa9d4ef12c44e480b60a346e00db12
出典データセット
uspto-grants-1997_11
特許番号
US05686456

反応ノート

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