2,4,5-Triphenylimidazole → 7-(1,2,4-Triphenyl-imidazolyl)-hept-5-ynoic acid

HRID 265390

반응식

HRID 265390 반응식
[C:1]1([C:7]2[NH:8][C:9](C3C=CC=CC=3)=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[OH-].[K+].Br[CH2:29][C:30]#[C:31][CH2:32][CH2:33][CH2:34][C:35]([O:37]C)=[O:36]>CN(C)C=O.CO>[C:1]1([N:8]2[C:9]([CH2:29][C:30]#[C:31][CH2:32][CH2:33][CH2:34][C:35]([OH:37])=[O:36])=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:11]=[C:7]2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

7

반응물 4

HCID 102322,4,5-TriphenylimidazoleHCID 14797Potassium HydroxideHCID 24758Sodium hydrideHCID 11287432Methyl 7-bromohept-5-ynoate

생성물 1

HCID 536889797-(1,2,4-Triphenyl-imidazolyl)-hept-5-ynoic acid

시약·촉매·용매 2

HCID 887Methanol용매HCID 6228Dimethylformamide용매

실험 절차

A solution of 2,4,5-triphenylimidazole (1.07 g) in dimethyl-formamide (20 ml) was treated with sodium hydride 50% in oil (0.17 g) and methyl 7-bromohept-5-ynoate (0.95 g). The solution was stirred for 18 hours when the solvent was removed under reduced pressure and the residue was chromatographed on silica gel eluted with chloroform-hexane to give a clear oil which was dissolved in methanol (20 ml) and treated with 10% potassium hydroxide solution (10 ml) for 2 hours. The methanol was removed under reduced pressure and the remaining aqueous was acidified (pH 3) and filtered. The filtrate was extracted with chloroform (3×50 ml). The chloroform extracts were dried over magnesium sulphate, filtered and the solvent removed to give a solid which was recrystallised from acetonitrile to give 7-(1,2,4-triphenyl-imidazolyl)-hept-5-ynoic acid as white prisms, m.p. 144°-145° C.; Found: C, 79.99; H, 5.81; N, 6.40% (C28H24N2O2);Requires: C, 79.97; H, 5.75; N, 6.66%

후처리

  1. customwas removed under reduced pressure
  2. customthe residue was chromatographed on silica gel
  3. washeluted with chloroform-hexane
  4. customto give a clear oil which
  5. customThe methanol was removed under reduced pressure
  6. filtrationfiltered
  7. extractionThe filtrate was extracted with chloroform (3×50 ml)
  8. dry with materialThe chloroform extracts were dried over magnesium sulphate
  9. filtrationfiltered
  10. customthe solvent removed
  11. customto give a solid which
  12. customwas recrystallised from acetonitrile

출처 및 근거

ORD 기록
ord-31e89f06d4824217bc472c262f066c8c
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05648373

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