Benzyl Bromide → 2-Phenylmethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

HRID 743437노트

반응식

HRID 743437 반응식
[CH:1]([CH:4]1[NH:8][S:7](=[O:10])(=[O:9])[NH:6][C:5]1=[O:11])(C)[CH3:2].[C:12]1([CH2:18]Br)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[C:20]1(C)C=CC=CC=1.CN(C=O)C>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:12]1([CH2:18][N:6]2[C:5](=[O:11])[CH:4]([CH2:1][CH2:2][CH3:20])[NH:8][S:7]2(=[O:10])=[O:9])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 194244514-Isopropyl-1,2,5-thiadiazolidin-3-one 1,1-dioxideHCID 21735183Dimethylformamide toluene

생성물 1

HCID 189222572-Phenylmethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide수율 72%

시약·촉매·용매 1

HCID 74236Tetrabutylammonium Bromide촉매

실험 절차

Eight grams (44.94 mmol) of 4-isopropyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide, phenylmethyl bromide (8.09 g, 47.2 mmol), and tetrabutylammonium bromide (1.5 g, 4.66 mmol) suspended in toluene/DMF (200 ml/50 ml) was allowed to react at 130° C. for 30 hours. The resulting mixture was cooled, the excess toluene was concentrated in vacuo, and the residue was diluted with 200 ml of water and extracted with ether/ethyl acetate (4:1, 700 ml). The organic layer was washed with water and brine, dried and concentrated in vacuo to yield a residue which was purified by flash chromatography to afford 8.6 g (72%) of 2-phenylmethyl-4-isopropyl-1,2,5-thiadiazol-idin-3-one 1,1-dioxide (Formula IX: R1 =H; R2 =isopropyl) as a solid.

후처리

  1. customto react at 130° C. for 30 hours
  2. temperatureThe resulting mixture was cooled
  3. concentrationthe excess toluene was concentrated in vacuo
  4. additionthe residue was diluted with 200 ml of water
  5. extractionextracted with ether/ethyl acetate (4:1, 700 ml)
  6. washThe organic layer was washed with water and brine
  7. customdried
  8. concentrationconcentrated in vacuo
  9. customto yield a residue which
  10. customwas purified by flash chromatography

출처 및 근거

ORD 기록
ord-8f905c599f9e42a5ae93696785f40892
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05556909

반응 노트

불러오는 중…