Sodium Hydroxide → 3-methyl-2-oxo-2,3-dihydro-1H-1,3-benzodiazole-5-carboxylic acid

HRID 2064261노트

반응식

HRID 2064261 반응식
[OH-].[Na+].[CH3:3][N:4]1[C:8]2[CH:9]=[C:10]([C:13]([O:15]C)=[O:14])[CH:11]=[CH:12][C:7]=2[NH:6][C:5]1=[O:17]>CO>[CH3:3][N:4]1[C:8]2[CH:9]=[C:10]([C:13]([OH:15])=[O:14])[CH:11]=[CH:12][C:7]=2[NH:6][C:5]1=[O:17]

참가 물질

4

반응물 2

HCID 14798Sodium Hydroxide2회HCID 67151300methyl 3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylate

생성물 1

HCID 671512733-methyl-2-oxo-2,3-dihydro-1H-1,3-benzodiazole-5-carboxylic acid수율 59.7%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
65 °C

실험 절차

Add 1N sodium hydroxide (6.1 mL, 6.1 mmol) to a suspension of methyl 3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylate (420 mg, 2.04 mmol) in methanol (10 mL). The suspension turned to a solution upon addition of 1N sodium hydroxide. Stir at 65° C. for 16 hours. Cool to room temperature then concentrate to remove the methanol. Extract the aqueous with ethyl acetate (5 mL). Acidify the aqueous with 2N hydrogen chloride (3 mL) to pH˜2. Concentrate the aqueous layer to a solid. Triturate the solid with water (3 mL). Filter the precipitate and dry under high vacuum to yield the title compound (234 mg, 59%) as a pale brown solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.28 (s, 3H), 7.01 (d, J=8.21 Hz, 1H), 7.57 (s, 1H), 7.63 (dd, J=8.11, 1.27 Hz, 1H), 11.19 (s, 1H), 12.60 (s, 1H).

후처리

  1. temperatureCool to room temperature
  2. concentrationthen concentrate
  3. customto remove the methanol
  4. extractionExtract the aqueous with ethyl acetate (5 mL)
  5. concentrationConcentrate the aqueous layer to a solid
  6. customTriturate the solid with water (3 mL)
  7. filtrationFilter the precipitate
  8. customdry under high vacuum

출처 및 근거

ORD 기록
ord-71fdae343a35485b979633ba51b6938b
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288405B2

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