Anthranilic acid, 3-hydroxy-, methyl ester → Methyl 2-amino-1,3-benzoxazole-4-carboxylate

HRID 249843

反応式

HRID 249843 の反応式
[N:1]1(C(N2C=CN=C2)N)C=CN=[CH:2]1.[CH3:13][O:14][C:15](=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[C:17]=1[NH2:23]>C1COCC1.CCOC(C)=O>[NH2:1][C:2]1[O:22][C:18]2[C:17](=[C:16]([C:15]([O:14][CH3:13])=[O:24])[CH:21]=[CH:20][CH:19]=2)[N:23]=1

参加物

5

反応物 2

HCID 205248Anthranilic acid, 3-hydroxy-, methyl esterHCID 66874404di(1H-imidazole-1-yl)methanamine

生成物 1

HCID 66873567Methyl 2-amino-1,3-benzoxazole-4-carboxylate収率 50%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of di(1H-imidazole-1-yl)methanamine (2.05 g, 12.26 mmol) in THF (60 mL) was added methyl-2-amino-3-hydroxybenzoate (1.98 g, 12.26 mmol) at room temperature and the resulting reaction mixture was heated to reflux for 17 h. The reaction mixture was cooled to room temperature, diluted with EtOAc (100 mL) and washed with H2O (3×100 mL), saturated ammonium chloride (2×100 mL), dried (Na2SO4), filtered and concentrated under reduced pressure. The crude material was purified by recrystallization from diethyl ether to afford methyl 2-aminobenzoxazole-4-carboxylate (1.10 g, 50%) as a brown solid. 1H NMR and MS consistent.

後処理

  1. customthe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureto reflux for 17 h
  4. washwashed with H2O (3×100 mL), saturated ammonium chloride (2×100 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude material was purified by recrystallization from diethyl ether

出典と根拠

ORDレコード
ord-0ed8eab141044d9a93ad410e4d2895c7
出典データセット
uspto-grants-2011_01
特許番号
US07863271B2

関連ノート

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