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Chloromethyl phenyl sulphide → 2-Phenylthiomethyl-4-(3-methylbutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

HRID 1736324
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HRID 1736324 반응식
[Cs].[CH3:2][CH:3]([CH3:15])[CH2:4][CH2:5][CH:6]1[N:10]([CH3:11])[S:9](=[O:13])(=[O:12])[NH:8][C:7]1=[O:14].[C:16]1([S:22][CH2:23]Cl)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CO.CN(C=O)C>[C:16]1([S:22][CH2:23][N:8]2[C:7](=[O:14])[CH:6]([CH2:5][CH2:4][CH:3]([CH3:15])[CH3:2])[N:10]([CH3:11])[S:9]2(=[O:13])=[O:12])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1
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참가 물질

5

반응물 2

HCID 81623Chloromethyl phenyl sulphideHCID 867492844-(3-Methylbutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide cesium salt

생성물 1

HCID 194244062-Phenylthiomethyl-4-(3-methylbutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide수율 70.6%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6228Dimethylformamide용매

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온도
85 °C

실험 절차

A mixture of 4-(3-methylbutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide cesium salt (prepared by reacting 7.7 g (34.95 mmol) of the compound of example 4(g) in methanol with 5.13 g of CS2CO3, followed by removal of the solvent and drying under high vacuum) and phenylthiomethyl chloride (6.65 g, 41.94 mmol) suspended in DMF was heated at 85° C. for 17 hours. The mixture was cooled, and poured into 300 ml of ice/water. The reaction mixture was extracted with ethyl acetate (3×) and the organic layer was washed with water and brine, and dried over sodium sulfate. The organic layer was concentrated in vacuo and the residue was purified by silica column chromatography (10% ethyl acetate in hexane) to afford 8.15 g (70.6%) of 2-phenylthiomethyl-4-(3-methylbutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula VI: R1 =H; R2 =(CH2)2CH(CH3)2 ; R3 =CH3) as a solid.

후처리

  1. customprepared
  2. customfollowed by removal of the solvent
  3. temperatureThe mixture was cooled
  4. extractionThe reaction mixture was extracted with ethyl acetate (3×)
  5. washthe organic layer was washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. concentrationThe organic layer was concentrated in vacuo
  8. customthe residue was purified by silica column chromatography (10% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-8633513babdd4d5981ded7079f39ed22
출처 데이터셋
uspto-grants-1996_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05541168

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