2,5-Dimethoxytetrahydrofuran → HCID 14962883, 화합물

HRID 274603노트

반응식

HRID 274603 반응식
[NH2:1][C:2]1[N:3]=[C:4]([CH2:12][CH2:13][CH3:14])[NH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].C([O-])(=O)C.[Na+].CO[CH:22]1[CH2:26][CH2:25][CH:24](OC)O1>C(O)(=O)C>[CH2:12]([C:4]1[NH:5][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:2]([N:1]2[CH:22]=[CH:26][CH:25]=[CH:24]2)[N:3]=1)[CH2:13][CH3:14]

참가 물질

5

반응물 3

HCID 790982,5-DimethoxytetrahydrofuranHCID 517045Sodium AcetateHCID 20093493ethyl 4-amino-2-propyl-1H-imidazole-5-carboxylate

생성물 1

HCID 14962883HCID 14962883, 화합물

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

A solution of ethyl 4-amino-2-propylimidazole-5-carboxylate from above (9.34 g, 47 mmol) and sodium acetate (23.2 g) in acetic acid (100 mL) was heated to reflux and treated with 2,5-dimethoxy-tetrahydrofuran (6.75 mL, 52 mmol). The reaction was held at reflux for 30 minutes, then cooled back to room temperature with an ice bath. The majority of the acetic acid was evaporated under reduced pressure, then the residue was partitioned between ethyl acetate and 10% aqueous K2CO3 (120 mL) each. The organic layer was dried over MgSO4 and evaporated. The residue was purified by flash chromatography on silica gel, eluting with CH2Cl2 -ethyl acetate (80:20). Evaporation of solvents gave a solid which was recrystallized from hexane/EtOAc (1:1) to give 7.4 g of the title compound, mp 134°-135° C.; MS (CI), 248 (m +1).

후처리

  1. temperatureto reflux
  2. temperatureat reflux for 30 minutes
  3. customThe majority of the acetic acid was evaporated under reduced pressure
  4. customthe residue was partitioned between ethyl acetate and 10% aqueous K2CO3 (120 mL) each
  5. dry with materialThe organic layer was dried over MgSO4
  6. customevaporated
  7. customThe residue was purified by flash chromatography on silica gel
  8. washeluting with CH2Cl2 -ethyl acetate (80:20)
  9. customEvaporation of solvents
  10. customgave a solid which
  11. customwas recrystallized from hexane/EtOAc (1:1)

출처 및 근거

ORD 기록
ord-7479a98218bd464a9071c382448dad5c
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05389661

반응 노트

불러오는 중…