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Methyl iodide → 3-(4-Chlorophenyl)-1,4-dimethyl-2-thia-1-azaspiro[4.5]dec-3-ene 2,2-dioxide

HRID 1245283
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HRID 1245283 반응식
[C:1]([C:4]1([NH:10][S:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)(=[O:13])=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)(=O)[CH3:2].[H-].[Na+].I[CH3:25]>CN(C=O)C>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([C:14]2[S:11](=[O:13])(=[O:12])[N:10]([CH3:25])[C:4]3([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]3)[C:1]=2[CH3:2])=[CH:16][CH:17]=1
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참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11461652N-(1-acetylcyclohexyl)-4-chlorophenyl-methanesulfonamide

생성물 1

HCID 113248403-(4-Chlorophenyl)-1,4-dimethyl-2-thia-1-azaspiro[4.5]dec-3-ene 2,2-dioxide수율 69%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
120 °C

실험 절차

N-(1-Acetylcyclohexyl)-4-chlorophenylmethane sulfonamide (1.02 g, 3.1 mmol) was dissolved in dry DMF (10 mL) under Ar. NaH (60%, 2.2 eq.) and iodomethane (2 eq.) were added and the mixture was stirred overnight at 120° C. After dilution with water the solution was extracted with ethyl acetate. The organic layer was washed with NaCl solution and water, dried (Na2SO4) and concentrated to yield 696 mg (69%) of the 3-(4-chlorophenyl)-1,4-dimethyl-2-thia-1-azaspiro[4.5]dec-3-ene 2,2-dioxide, shown below as a solid. MS (IS): 326 [MH]+.

후처리

  1. extractionAfter dilution with water the solution was extracted with ethyl acetate
  2. washThe organic layer was washed with NaCl solution and water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-f9c9e13e5c1d4691b2a67b92135c7667
출처 데이터셋
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07125840B2

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