Ethyl Acetate → methyl 3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylate

HRID 2281904ノート

反応式

HRID 2281904 の反応式
[C:1](C1NC=CN=1)(C1NC=CN=1)=[O:2].[NH2:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][C:15]=1[NH:24][CH3:25].C(OCC)(=O)C>O1CCCC1>[CH3:25][N:24]1[C:15]2[CH:16]=[C:17]([C:18]([O:20][CH3:21])=[O:19])[CH:22]=[CH:23][C:14]=2[NH:13][C:1]1=[O:2]

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 5250894Bis-(1H-imidazol-2-YL)-methanone2 回HCID 57835341Methyl 4-amino-3-(methylamino)benzoate

生成物 1

HCID 67151300methyl 3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylate収率 64.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Add carbonyl diimidazole (567 mg, 3.50 mmol) to a solution of methyl 4-amino-3-(methylamino)benzoate (586 mg, 3.19 mmol) in tetrahydrofuran (20 mL) at room temperature. Stir the yellow solution at room temperature for 16 hours. Add carbonyl diimidazole (500 mg, 0.96). Stir at room temperature for 4 hours. Add ethyl acetate (75 mL). Wash with 10% citric acid (5 mL), 1N sodium hydroxide (5 mL), and brine (5 mL). Dry the organics over magnesium sulfate, filter, concentrate, and dry under high vacuum to yield a crude yellow solid (690 mg, 100%). Triturate this crude solid with ethyl acetate (10 mL). Filter the precipitate and dry under high vacuum to yield methyl 3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylate (422 mg, 64%). 1H NMR (400 MHz, CDCl3) δ ppm 3.46 (s, 3 H), 3.92 (s, 3 H), 7.12 (d, J=8.21 Hz, 1 H), 7.68 (s, 1 H), 7.84 (dd, J=8.31, 1.47 Hz, 1 H), 9.87-10.03 (m, 1 H).

後処理

  1. stirringStir at room temperature for 4 hours
  2. washWash with 10% citric acid (5 mL), 1N sodium hydroxide (5 mL), and brine (5 mL)
  3. dry with materialDry the organics over magnesium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customdry under high vacuum
  7. customto yield a crude yellow solid (690 mg, 100%)
  8. customTriturate this crude solid with ethyl acetate (10 mL)
  9. filtrationFilter the precipitate
  10. customdry under high vacuum

出典と根拠

ORDレコード
ord-e67be214933c421c832c991513a414f0
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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