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

HRID 440883노트

반응식

HRID 440883 반응식
[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

참가 물질

6

반응물 4

HCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 21476408p-Bromobenzamidine benzenesulfonateHCID 54209384HCID 54209384, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-809cfc024d9242bba2e9cff0ec6eb91c
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05521189

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