Formaldehyde → 2,2-Dimethyl-6-(1H-imidazol-1-YL)benzopyran

HRID 36616

반응식

HRID 36616 반응식
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9]([CH3:12])([CH3:11])[CH:8]=[CH:7][C:6]=2[CH:13]=1.[C:14]([O-])(=O)[CH3:15].[NH4+:18].[CH2:19]=O.C(C=O)=O.[OH-].[NH4+]>C(O)(=O)C.CO>[CH3:12][C:9]1([CH3:11])[CH:8]=[CH:7][C:6]2[CH:13]=[C:2]([N:1]3[CH:15]=[CH:14][N:18]=[CH:19]3)[CH:3]=[CH:4][C:5]=2[O:10]1

참가 물질

8

반응물 5

HCID 712FormaldehydeHCID 7860GlyoxalHCID 14923Ammonium HydroxideHCID 517165Ammonium AcetateHCID 100808812,2-Dimethyl-2H-chromen-6-amine

생성물 1

HCID 199376002,2-Dimethyl-6-(1H-imidazol-1-YL)benzopyran

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 887Methanol용매

반응 조건

온도
65 °C

실험 절차

To a stirred solution of 20 g (0.11 mol) of 6-amino-2,2-dimethylbenzopyran and 70 g (0.91 mol) of ammonium acetate in 190 mL of acetic acid and 770 mL of MeOH at 65° C. is added dropwise over 0.5 h, a mixture of 11.1 g (0.14 mol) of formaldehyde and 20g (0.14 mol) of glyoxal. The mixture is stirred for 1 hour at 65° C., then poured onto 800 g of ice. The pH of the solution is adjusted to 10 by the addition of concentrated ammonium hydroxide. The mixture is extracted with dichloromethane (3×200 mL) and the combined organic extracts are dried with sodium sulfate, filtered and evaporated under reduced pressure. The resulting oil is subjected to chromatography on silica gel utilizing 3% methanol in dichloromethane as eluent. The eluates are analyzed utilizing thin layer chromatography and appropriate fractions are combined and evaporated to produce the title compound.

후처리

  1. extractionThe mixture is extracted with dichloromethane (3×200 mL)
  2. dry with materialthe combined organic extracts are dried with sodium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customevaporated

출처 및 근거

ORD 기록
ord-90b75e363fa247b8ab5b0c4afb592cd3
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05416097

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