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

HRID 80237

反応式

HRID 80237 の反応式
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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 962Water溶媒HCID 6212Chloroform溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6ccde38690344d719845525f28fd3293
出典データセット
uspto-grants-2014_09
特許番号
USRE045173E1

関連ノート

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