Sodium Chloride → HCID 54126959、化合物

HRID 1250203ノート

反応式

HRID 1250203 の反応式
[CH3:1][C:2]1[N:3]=[N:4][S:5][C:6]=1[CH:7]=O.[C:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])#[N:10].N1CCCC1.S(C1C=CC(C)=CC=1)(O)(=O)=O.[Cl-].[Na+]>C1(C)C=CC=CC=1>[C:9]([C:11](=[CH:7][C:6]1[S:5][N:4]=[N:3][C:2]=1[CH3:1])[C:12]([O:14][CH2:15][CH3:16])=[O:13])#[N:10]

参加物

7

反応物 5

HCID 5234Sodium ChlorideHCID 6101p-Toluenesulfonic acidHCID 7764Ethyl cyanoacetateHCID 31268PyrrolidineHCID 27712924-Methyl-1,2,3-thiadiazole-5-carbaldehyde

生成物 1

HCID 54126959HCID 54126959、化合物収率 30%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To 50 ml of toluene were added 1.5 g (12 mmol) of 4-methyl-1,2,3-thiadiazole-5-carbaldehyde, 1.5 g (13 mmol) of ethyl cyanoacetate, 0.40 g (6.0 mmol) of pyrrolidine and 0.20 g (1.2 mmol) of tosylic acid. In a reactor equipped with a Dean-Stark dehydrating apparatus, the mixture obtained above was stirred for 2 hours with heating under reflux. After the reaction was completed, a saturated aqueous solution of sodium chloride was added to the reaction mixture, the objective product was extracted with ethyl acetate, the organic layer was washed successively with dilute hydrochloric acid, saturated aqueous solution of sodium hydrogen carbonate and saturated aqueous solution of sodium chloride, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography using 3:1 mixture of n-hexane and ethyl acetate. Thus, 0.73 g of the objective compound was obtained.

後処理

  1. customIn a reactor equipped with a Dean-Stark
  2. customthe mixture obtained
  3. temperaturewith heating
  4. temperatureunder reflux
  5. extractionthe objective product was extracted with ethyl acetate
  6. washthe organic layer was washed successively with dilute hydrochloric acid, saturated aqueous solution of sodium hydrogen carbonate and saturated aqueous solution of sodium chloride
  7. distillationthe solvent was distilled off under reduced pressure
  8. customthe residue was purified by silica gel column chromatography
  9. addition3:1 mixture of n-hexane and ethyl acetate

出典と根拠

ORDレコード
ord-84bab6e52ba347f3bac7f89f821b4d13
出典データセット
uspto-grants-2002_01
特許番号
US06337341B1

反応ノート

読み込み中…