Methanol → 3-(3-Benzothiazol-6-yl-2-oxo-imidazolidin-1-yl)-pyridine-4-carbaldehyde

HRID 2383923

반응식

HRID 2383923 반응식
CC1C=CC(S(O)(=O)=O)=CC=1.[S:12]1[C:16]2[CH:17]=[C:18]([N:21]3[CH2:25][CH2:24][N:23]([C:26]4[CH:27]=[N:28][CH:29]=[CH:30][C:31]=4[CH:32](OC)[O:33]C)[C:22]3=[O:37])[CH:19]=[CH:20][C:15]=2[N:14]=[CH:13]1.CO>CC(C)=O.O.C(Cl)(Cl)Cl>[S:12]1[C:16]2[CH:17]=[C:18]([N:21]3[CH2:25][CH2:24][N:23]([C:26]4[CH:27]=[N:28][CH:29]=[CH:30][C:31]=4[CH:32]=[O:33])[C:22]3=[O:37])[CH:19]=[CH:20][C:15]=2[N:14]=[CH:13]1

참가 물질

7

반응물 3

HCID 887MethanolHCID 6101p-Toluenesulfonic acidHCID 498724521-Benzothiazol-6-yl-3-(4-dimethoxymethyl-pyridin-3-yl)-imidazolidin-2-one

생성물 1

HCID 596362723-(3-Benzothiazol-6-yl-2-oxo-imidazolidin-1-yl)-pyridine-4-carbaldehyde수율 99.5%

시약·촉매·용매 3

HCID 180Acetone용매HCID 962Water용매HCID 6212Chloroform용매

실험 절차

PTSA (2.2 g, 11.672 mmol) was added to a stirred solution of 1-benzothiazol-6-yl-3-(4-dimethoxymethyl-pyridin-3-yl)-imidazolidin-2-one (I-177a: 460 mg, 1.2418 mmol) in acetone (20 mL) and water (20 mL). The resulting reaction mass was stirred for 48 hours at room temperature. The reaction was monitored by TLC (5% methanol in chloroform). The reaction mixture was concentrated, the residue was diluted with ice-water, basified with saturated NaHCO3 solution and extracted using ethyl acetate. The aqueous layer was filtered and the solid collected was dried under reduced pressure. The solid was dissolved in methanol and chloroform, dried over Na2SO4 and concentrated under reduced pressure to afford 400 mg of the product (99.5% yield).

후처리

  1. customThe resulting reaction mass
  2. concentrationThe reaction mixture was concentrated
  3. additionthe residue was diluted with ice-water
  4. extractionextracted
  5. filtrationThe aqueous layer was filtered
  6. customthe solid collected
  7. customwas dried under reduced pressure
  8. dissolutionThe solid was dissolved in methanol
  9. dry with materialchloroform, dried over Na2SO4
  10. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-73b9021cf1714944acb1183ab0fcd82f
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263635B2

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