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

HRID 2281905ノート

反応式

HRID 2281905 の反応式
[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]

参加物

4

反応物 2

HCID 14798Sodium Hydroxide2 回HCID 67151300methyl 3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylate

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
65 °C

実験手順

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, 3 H), 7.01 (d, J=8.21 Hz, 1 H), 7.57 (s, 1 H), 7.63 (dd, J=8.11, 1.27 Hz, 1 H), 11.19 (s, 1 H), 12.60 (s, 1 H).

後処理

  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

出典と根拠

ORDレコード
ord-ec387487f8284044ae55d4ad102719d1
出典データセット
uspto-grants-2015_09
特許番号
US09139587B2

反応ノート

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