Methyl iodide → 3-benzyl-4-methyl-1,2,4-oxadiazol-5(4H)-one

HRID 1076955노트

반응식

HRID 1076955 반응식
[C:1]1([CH2:7][C:8]2[NH:12][C:11](=[O:13])[O:10][N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:14][O-].[Na+].CI>CO>[CH3:14][N:12]1[C:11](=[O:13])[O:10][N:9]=[C:8]1[CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 10942334Sodium MethoxideHCID 1356776173-Benzyl-1,2,4-oxadiazol-5(2H)-one

생성물 1

HCID 215353933-benzyl-4-methyl-1,2,4-oxadiazol-5(4H)-one

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

35.2 g. (0.2 moles) of 3-(phenylmethyl)-1,2,4-oxadiazol-5(4H)-one obtained in Example 1 (a) are dissolved in 100 ml of methanol and 110 ml. (0.22 moles) of 2N sodium methylate solution are added. The solution is evaporated to dryness and the residue is dissolved in 200 ml. of anhydrous dimethylformamide. 35.5 g. (0.25 moles) of methyl iodide are added dropwise while cooling with ice water and stirring. The reaction mixture warms slightly and is stirred overnight at room temperature. The reaction mixture is concentrated and the residue is treated with water and acidified with 2N hydrochloric acid. The crystals are filtered under suction, triturated with sodium bicarbonate solution while still moist, again filtered under suction, and washed with water. 33.6 g. of 4-methyl-3-(phenylmethyl)-1,2,4-oxadiazol-5(4H)-one are obtained, m.p. 105°-107°. After recrystallizing twice from isopropanol the m.p. is 110°-112°.

후처리

  1. customThe solution is evaporated to dryness
  2. dissolutionthe residue is dissolved in 200 ml
  3. stirringis stirred overnight at room temperature
  4. concentrationThe reaction mixture is concentrated
  5. additionthe residue is treated with water
  6. filtrationThe crystals are filtered under suction
  7. customtriturated with sodium bicarbonate solution while still moist,
  8. filtrationagain filtered under suction
  9. washwashed with water

출처 및 근거

ORD 기록
ord-3fa8c5cfef064887bf40e54eb098e2fd
출처 데이터셋
uspto-grants-1976_05
특허 번호
US03959259

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