Chloromethyl phenyl sulphide → 2-Phenylthiomethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

HRID 743420노트

반응식

HRID 743420 반응식
[CH2:1]([CH:4]1[NH:8][S:7](=[O:10])(=[O:9])[NH:6][C:5]1=[O:11])[CH2:2][CH3:3].[C:12]1([S:18][CH2:19]Cl)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1(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][CH3:3])[NH:8][S:7]2(=[O:9])=[O:10])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

5

반응물 2

HCID 81623Chloromethyl phenyl sulphideHCID 189222484-Propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

생성물 1

HCID 194244652-Phenylthiomethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide수율 63%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 1140Toluene용매

실험 절차

To a mixture of 4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (5.1 g, 28.65 mmol)suspended in 210 ml of toluene was added phenylthiomethyl chloride (4.93 g, 31.49 mmol) and tetrabutylammonium bromide (0.92 g, 2.86 mmol). The resulting mixture was refluxed for 18 hours, cooled, filtered, and the filtrate was concentrated in vacuo. The residue was purified by column chromatography to afford 5.39 g (63%) of 2-phenylthiomethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula VI: R1 =H; R2 =propyl; R3 =H).

후처리

  1. temperatureThe resulting mixture was refluxed for 18 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-091ec06c42eb402eafb47269a8e00dc0
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05556909

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