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

HRID 839949

反応式

HRID 839949 の反応式
[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

参加物

5

反応物 4

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

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4dbd8545403e47a9b16ec79e12993c80
出典データセット
uspto-grants-1978_06
特許番号
US04097669

関連ノート

読み込み中…