Benzene → (4-Methyl-1,2,3-thiadiazol-5-yl)(phenyl)methanone

HRID 636662

反応式

HRID 636662 の反応式
S(Cl)(Cl)=O.[CH3:5][C:6]1[N:7]=[N:8][S:9][C:10]=1[C:11]([OH:13])=O.[Cl-].[Al+3].[Cl-].[Cl-].[CH:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[C:11]([C:10]1[S:9][N:8]=[N:7][C:6]=1[CH3:5])(=[O:13])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

5

反応物 4

HCID 241BenzeneHCID 24386Thionyl ChlorideHCID 13819924-Methyl-1,2,3-thiadiazole-5-carboxylic acidHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 12298991(4-Methyl-1,2,3-thiadiazol-5-yl)(phenyl)methanone収率 97%

実験手順

To 2.0 g (15 mimol) of thionyl chloride was added 0.50 g (3.5 mmol) of 4-methyl-1,2,3-thiadiazole-5-carboxylic acid. After heating the mixture with stirring for 2 hours, the thionyl chloride was distilled off under reduced pressure, and the residue was added to a solution of 1.8 g (15 mmol) of aluminum chloride in 20 ml benzene and made to react with heating for 3 hours. After the reaction was completed, the reaction mixture was poured into ice water, the objective product was extracted with ethyl acetate, the organic layer was ashed with a saturated aqueous solution of sodium chloride and dried, the solvent was distilled off under educed pressure, and the residue was purified by silica gel column chromatography using 4:1 mixture of n-hexane and ethyl acetate. Thus, 0.69 g of the objective compound was obtained.

後処理

  1. temperatureAfter heating the mixture
  2. distillationthe thionyl chloride was distilled off under reduced pressure
  3. customto react
  4. temperaturewith heating for 3 hours
  5. extractionthe objective product was extracted with ethyl acetate
  6. customdried
  7. distillationthe solvent was distilled off
  8. customthe residue was purified by silica gel column chromatography
  9. addition4:1 mixture of n-hexane and ethyl acetate

出典と根拠

ORDレコード
ord-2b7872b2bf45499d919201ef99717658
出典データセット
uspto-grants-2001_02
特許番号
US06194444B1

関連ノート

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