Sodium Iodide → Ethyl 2-[(3-acetoxy-2-oxopropan-1-yl)(2-nitrobenzenesulfonyl)amino]acetate

HRID 1244794

반응식

HRID 1244794 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])(=[O:12])=[O:11])([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[C:28]([O:31][CH2:32][C:33]([CH2:35]Cl)=[O:34])(=[O:30])[CH3:29]>CN(C)C=O.O>[C:28]([O:31][CH2:32][C:33](=[O:34])[CH2:35][N:13]([S:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])(=[O:12])=[O:11])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])(=[O:30])[CH3:29]

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 384132-Propanone, 1-(acetyloxy)-3-chloro-HCID 3454399Ethyl 2-(2-nitrobenzenesulfonamido)acetate

생성물 1

HCID 21922543Ethyl 2-[(3-acetoxy-2-oxopropan-1-yl)(2-nitrobenzenesulfonyl)amino]acetate수율 67.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

실험 절차

To a suspension of the compound obtained in Step 1 (10.0 g), potassium carbonate (7.20 g) and sodium iodide (5.2 g) in N,N-dimethylformamide (100 ml) was added a solution (20 ml) of 1-acetoxy-3-chloroacetone (7.84 g) in N,N-dimethylformamide under cooling with ice and the mixture was stirred at room temperature for 2 hours. Water was added to the reaction mixture under cooling with ice, followed by extraction with ethyl acetate. The organic layer was washed with saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. To the resulting residue was added hexane and the mixture was stirred. The supernatant was removed by decantation and crystallized by addition of diethyl ether. The crystals were collected by filtration and air-dried to thereby obtain the title compound (9.36 g). NMR spectrum (*CDCl3) δppm: 8.10–8.02 (1H, m), 7.76–7.62 (3H, m), 4.73 (2H, s), 4.53 (2H, s), 4.24 (2H, s), 4.15 (2H, q, J=7 Hz), 2.16 (3H, s), 1.24 (3H, t, J=7 Hz)

후처리

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. additionTo the resulting residue was added hexane
  8. stirringthe mixture was stirred
  9. customThe supernatant was removed by decantation
  10. customcrystallized by addition of diethyl ether
  11. filtrationThe crystals were collected by filtration
  12. customair-dried

출처 및 근거

ORD 기록
ord-9221d69f4f3e44739f04b9310a1eb089
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07122662B2

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