Water → methyl 2-chloro-1H-1,3-benzodiazole-7-carboxylate

HRID 43810노트

반응식

HRID 43810 반응식
P(Cl)(Cl)([Cl:3])=O.O=[C:7]1[NH:11][C:10]2[CH:12]=[CH:13][CH:14]=[C:15]([C:16]([O:18][CH3:19])=[O:17])[C:9]=2[NH:8]1.O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.C1COCC1>[Cl:3][C:7]1[NH:11][C:10]2[CH:12]=[CH:13][CH:14]=[C:15]([C:16]([O:18][CH3:19])=[O:17])[C:9]=2[N:8]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 22745204Methyl 2-oxo-2,3-dihydro-1H-benzo[d]imidazole-4-carboxylate

생성물 1

HCID 68407476methyl 2-chloro-1H-1,3-benzodiazole-7-carboxylate수율 70.9%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
85 °C

실험 절차

Phosphorus oxychloride (8.5 g, 55.6 mmol) was added to methyl 2-oxo-2,3-dihydro-1H-benzimidazole-4-carboxylate (1.03 g, 5.36 mmol) (reference: WO 2006/116412 A2), and the mixture was stirred at 85° C. for four hours. The reaction solution was diluted with ethyl acetate and THF, slowly added to cold water and neutralized with sodium bicarbonate. The separated organic layer was washed with brine and dried over anhydrous sodium sulfate. Following concentration under reduced pressure, the residue was dissolved in toluene and the insoluble matter was removed. Concentration under reduced pressure gave 800 mg of the title compound as an oily substance. The resulting compound was used for the next reaction without purification.

후처리

  1. washThe separated organic layer was washed with brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentration under reduced pressure
  4. dissolutionthe residue was dissolved in toluene
  5. customthe insoluble matter was removed
  6. concentrationConcentration under reduced pressure

출처 및 근거

ORD 기록
ord-1d427edb06c84a3bbcf90349f410268a
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536197B2

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