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Methyl iodide → 3-Methyl-5-[2-[(phenylmethyl)thio]phenyl]-1,3,4-oxadiazol-2(3H)-one

HRID 255824
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HRID 255824 반응식
[CH3:1]C(C)([O-])C.[K+].[C:7]1([CH2:13][S:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]2[O:25][C:24](=[O:26])[NH:23][N:22]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CI>CN(C=O)C>[CH3:1][N:23]1[N:22]=[C:21]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[S:14][CH2:13][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:25][C:24]1=[O:26]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 139588535-{2-[(Phenylmethyl)thio]phenyl}-1,3,4-oxadiazol-2(3H)-oneHCID 23665647Potassium tert-butoxide

생성물 1

HCID 139588543-Methyl-5-[2-[(phenylmethyl)thio]phenyl]-1,3,4-oxadiazol-2(3H)-one수율 68.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
25 °C

실험 절차

To a suspension of 2.9 g of potassium t-butoxide in 60 ml of DMF under a N2 atmosphere was added portionwise 7 g of the product of Example 1 while maintaining the reaction temperature at 25°-30° C. with an ice-water bath. After stirring at 25° C. for 1 hour, 7 g of methyl iodide was added dropwise to cause an exotherm to 37° C. The suspension was heated at 40°-60° C. for 5 hours, then cooled to 25° and poured onto excess ice-water to yield a precipitate. The suspension was filtered, and the isolated solid was dissolved in tetrahydrofuran and dried over MgSO4. The isolated solid was passed through a silica gel column with methylene chloride and, after evaporation of the first eluant, 5 g of the subject compound was obtained; m.p. 137°-140° C.

후처리

  1. temperaturewhile maintaining the reaction temperature at 25°-30° C. with an ice-water bath
  2. customto 37° C
  3. temperatureThe suspension was heated at 40°-60° C. for 5 hours
  4. temperaturecooled to 25°
  5. customto yield a precipitate
  6. filtrationThe suspension was filtered
  7. dissolutionthe isolated solid was dissolved in tetrahydrofuran
  8. dry with materialdried over MgSO4
  9. customafter evaporation of the first eluant

출처 및 근거

ORD 기록
ord-a0fbf1951fcb44e4b5b2b3b7c1e13f43
출처 데이터셋
uspto-grants-1987_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04699647

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