p-Toluenesulfonic acid → HCID 54126959, 화합물

HRID 636671노트

반응식

HRID 636671 반응식
[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.[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]

참가 물질

7

반응물 5

HCID 6101p-Toluenesulfonic acidHCID 7764Ethyl cyanoacetateHCID 31268PyrrolidineHCID 27712924-Methyl-1,2,3-thiadiazole-5-carbaldehydeHCID 5360545Sodium

생성물 1

HCID 54126959HCID 54126959, 화합물수율 30%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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 Achloride 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.

후처리

  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

출처 및 근거

ORD 기록
ord-4cbf54cf4f8d4370bcf243985507cb48
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06194444B1

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