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

HRID 80237

Reaction equation

HRID 80237 reaction equation
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

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-6ccde38690344d719845525f28fd3293
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Linked notes

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