Methyl iodide → 2-Phenylmethyl-4-propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

HRID 743438노트

반응식

HRID 743438 반응식
[CH3:1]C(C)([O-])C.[K+].[C:7]1([CH2:13][N:14]2C(=O)[CH:17](C(C)C)[NH:16][S:15]2(=[O:24])=[O:23])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CI.[CH2:27]1[CH2:31][O:30][CH2:29][CH2:28]1>>[C:7]1([CH2:13][N:14]2[C:29](=[O:30])[CH:28]([CH2:27][CH2:31][CH3:1])[N:16]([CH3:17])[S:15]2(=[O:24])=[O:23])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

참가 물질

5

반응물 4

HCID 6328Methyl iodideHCID 8028Tetrahydrofuran2회HCID 23665647Potassium tert-butoxideHCID 542672972-Phenylmethyl-4-isopropyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

생성물 1

HCID 189222542-Phenylmethyl-4-propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide수율 88%

실험 절차

To a solution of potassium t-butoxide (3.53 g, 29 mmol) in THF was added a solution of 2-phenylmethyl-4-isopropyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (7.7 g, 29 mmol) in THF at 0° C and the mixture was stirred at this temperature for 1 hour. To the mixture was added methyl iodide (20.38 g, 0. 143 mol) and the resulting mixture was allowed to stir at room temperature for 2.5 hours. The resulting mixture was quenched with brine, extracted with ether, and the organic layer was washed with brine. The organic layer was dried, concentrated in vacuo, and the residue was purified by flash chromatography to afford 7.1 g (88%) of 2-phenylmethyl-4-isopropyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula XI: R1 =H; R2 =isopropyl, R3 =methyl) as a solid, m.p. 52.5°-54° C.

후처리

  1. stirringto stir at room temperature for 2.5 hours
  2. customThe resulting mixture was quenched with brine
  3. extractionextracted with ether
  4. washthe organic layer was washed with brine
  5. customThe organic layer was dried
  6. concentrationconcentrated in vacuo
  7. customthe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-4836984d84a2415785cf7a69a7effcb2
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05556909

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