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

HRID 743438ノート

反応式

HRID 743438 の反応式
[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

参加物

5

反応物 4

HCID 6328Methyl iodideHCID 8028Tetrahydrofuran2 回HCID 23665647Potassium tert-butoxideHCID 542672972-Phenylmethyl-4-isopropyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4836984d84a2415785cf7a69a7effcb2
出典データセット
uspto-grants-1996_09
特許番号
US05556909

反応ノート

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