P-Toluenesulfonamide → 1,3-Dimethyl-5-tosyl-5,6-dihydro-4H-thieno[3,4-c]pyrrole

HRID 1769085

반응식

HRID 1769085 반응식
Cl[CH2:2][C:3]1[C:7]([CH2:8]Cl)=[C:6]([CH3:10])[S:5][C:4]=1[CH3:11].[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18]([NH2:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:11][C:4]1[S:5][C:6]([CH3:10])=[C:7]2[CH2:8][N:21]([S:18]([C:15]3[CH:16]=[CH:17][C:12]([CH3:22])=[CH:13][CH:14]=3)(=[O:19])=[O:20])[CH2:2][C:3]=12

참가 물질

5

반응물 3

HCID 6269P-ToluenesulfonamideHCID 11430Potassium CarbonateHCID 2883993,4-Bis(chloromethyl)-2,5-dimethylthiophene

생성물 1

HCID 189470571,3-Dimethyl-5-tosyl-5,6-dihydro-4H-thieno[3,4-c]pyrrole수율 63.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

A solution of 10 g (0.048 mol) of 3,4-bis(chloromethyl)-2,5-dimethylthiophene and 8.22 g of p-toluenesulphonamide in 600 ml of dry dimethylformamide is added dropwise, over 6 h, to a stirred suspension, heated to 100°-110° C., of 180 g of potassium carbonate in 900 ml of dimethylformamide. After the end of the addition, the mixture is maintained at the same temperature for 30 min, and then filtered. The solid is washed with dimethylformamide. The filtrate is concentrated under vacuum, and the residue is treated with 100 ml of ethanol, and filtered. The solid residue remaining is washed with ethanol and dried. 9.39 g of product are obtained. Melting point: 163°-164° C.

후처리

  1. additionAfter the end of the addition
  2. temperaturethe mixture is maintained at the same temperature for 30 min
  3. filtrationfiltered
  4. washThe solid is washed with dimethylformamide
  5. concentrationThe filtrate is concentrated under vacuum
  6. additionthe residue is treated with 100 ml of ethanol
  7. filtrationfiltered
  8. washThe solid residue remaining is washed with ethanol
  9. customdried

출처 및 근거

ORD 기록
ord-32ddc447f8a04f45a562d00df4e39c31
출처 데이터셋
uspto-grants-1995_01
특허 번호
US05380742

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