Toluene → 2-Phenylthiomethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

HRID 743425노트

반응식

HRID 743425 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([S:18][CH2:19]Cl)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[C:21]1(C)C=CC=CC=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:12]1([S:18][CH2:19][N:6]2[C:5](=[O:11])[CH:4]([CH2:1][CH2:2][CH3:21])[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 1140TolueneHCID 81623Chloromethyl phenyl sulphideHCID 194244514-Isopropyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

생성물 1

HCID 194244652-Phenylthiomethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

시약·촉매·용매 1

HCID 74236Tetrabutylammonium Bromide촉매

실험 절차

To a mixture of 4-isopropyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (7.0 g, 39.32 mmol) suspended in 150 ml of toluene was added phenylthiomethyl chloride (6.83 g, 43 mmol) and tetrabutylammonium bromide (1.26 g, 3.93 mmol). The resulting mixture was refluxed for 17 hours, cooled, filtered, and the filtrate was concentrated in vacuo. The residue was purified by column chromatography to afford 5.2 g of 2-phenylthiomethyl-4-isopropyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula VI: R1 =H; R2 =isopropyl; R3 =H).

후처리

  1. temperatureThe resulting mixture was refluxed for 17 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-7091787311fc43e8b1b57e5c95b7bbac
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05556909

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