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

HRID 249843

반응식

HRID 249843 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0ed8eab141044d9a93ad410e4d2895c7
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863271B2

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