Tetrahydrofuran → 2-[(3,5-Dimethylphenyl)sulfanyl]-5-(trifluoromethyl)-1,3,4-thiadiazole

HRID 839949

반응식

HRID 839949 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([SH:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.C(N(CC)CC)C.Br[C:18]1[S:19][C:20]([C:23]([F:26])([F:25])[F:24])=[N:21][N:22]=1.O1CCCC1>>[CH3:1][C:2]1[CH:3]=[C:4]([S:9][C:18]2[S:19][C:20]([C:23]([F:26])([F:25])[F:24])=[N:21][N:22]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1

참가 물질

5

반응물 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 1175483,5-DimethylbenzenethiolHCID 128746852-Bromo-5-(trifluoromethyl)-1,3,4-thiadiazole

생성물 1

HCID 203228922-[(3,5-Dimethylphenyl)sulfanyl]-5-(trifluoromethyl)-1,3,4-thiadiazole수율 95%

실험 절차

8.5 g (0.061 mole) of 3,5-dimethylthiophenol, 6.2 g (0.061 mole) of triethylamine and 14.3 g (0.061 mole) of 2 -bromo-5-trifluoromethyl-1,3,4-thiadiazole in 150 mole of tetrahydrofuran were stirred for 30 minutes under reflux. The salt (by-product) which had precipitated was filtered off and washed thoroughly with tetrahydrofuran. After distilling off the solvent in vacuo, a colorless oil passed over on distillation. 16.8 g (95% of theory) of 2-(3',5'-dimethylphenylthio)-5-trifluoromethyl-1,3,4-thiadiazole of boiling point 107°-108° C/10.2 mm Hg were obtained. 22.8 g (0.201 mole) of hydrogen peroxide (30% strength) in 100 ml of glacial acetic acid were added thereto and the reaction mixture was stirred for 15 hours at 60° C, and poured onto ice water. The precipitate was filtered off and recrystallized from ethanol. 12.7 g (54% of theory) of 2-(3',5'-dimethylphenylsulfonyl)-5-trifluoromethyl-1,3,4-thiadiazole of melting point 110° C were obtained.

후처리

  1. temperatureunder reflux
  2. customThe salt (by-product) which had precipitated
  3. filtrationwas filtered off
  4. washwashed thoroughly with tetrahydrofuran
  5. distillationAfter distilling off the solvent in vacuo
  6. distillationa colorless oil passed over on distillation

출처 및 근거

ORD 기록
ord-4dbd8545403e47a9b16ec79e12993c80
출처 데이터셋
uspto-grants-1978_06
특허 번호
US04097669

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