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Sulfolane → 7-fluoro-2-heptylthio-6-methyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one

HRID 1073784
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HRID 1073784 반응식
Cl[C:2]1[N:3]=[C:4]2[S:12][C:11]([S:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[N:10][N:5]2[C:6](=[O:9])[C:7]=1[CH3:8].[F-:21].[K+].S1(CCCC1)(=O)=O>O>[F:21][C:2]1[N:3]=[C:4]2[S:12][C:11]([S:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[N:10][N:5]2[C:6](=[O:9])[C:7]=1[CH3:8]
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참가 물질

5

반응물 3

HCID 31347SulfolaneHCID 522689Potassium FluorideHCID 156107877-chloro-2-heptylthio-6-methyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one

생성물 1

HCID 156107887-fluoro-2-heptylthio-6-methyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one수율 63%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A solution of 8.6 g of the thus obtained 7-chloro-2-heptylthio-6-methyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one, 3.0 g of spray dry potassium fluoride and 32 ml of sulfolane was heated at 205°~225° C. in a stream of nitrogen for 1 and half hours. After cooling, water was added to the mixture, and the mixture was extracted with toluene. The toluene layer was collected and washed with water. The toluene phase was dried over anhydrous sodium sulfate, the solvent was distilled off. The residue was purified by column chromatography on a silica gel column with an ethyl acetate/n-hexane (1:3) mixture as an eluent. After the solvent was distilled off, 5.2 g of 7-fluoro-2-heptylthio-6-methyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one was obtained. m.p. 78°~91° C. Yield 63%.

후처리

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with toluene
  3. customThe toluene layer was collected
  4. washwashed with water
  5. dry with materialThe toluene phase was dried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off
  7. customThe residue was purified by column chromatography on a silica gel column with an ethyl acetate/n-hexane (1:3) mixture as an eluent
  8. distillationAfter the solvent was distilled off

출처 및 근거

ORD 기록
ord-480f7532f15b4be5b83f9acd01d4c3bb
출처 데이터셋
uspto-grants-1990_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04971971

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