(S)-4-methylbenzenesulfinamide → (NE,S)-4-methyl-N-[(5-nitro-2-propan-2-ylsulfanylphenyl)methylidene]benzenesulfinamide

HRID 272784노트

반응식

HRID 272784 반응식
[CH:1]([S:4][C:5]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:6]=1[CH:7]=O)([CH3:3])[CH3:2].[C:16]1([CH3:25])[CH:21]=[CH:20][C:19]([S@@:22]([NH2:24])=[O:23])=[CH:18][CH:17]=1>C(Cl)Cl>[CH:1]([S:4][C:5]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:6]=1/[CH:7]=[N:24]/[S@:22]([C:19]1[CH:20]=[CH:21][C:16]([CH3:25])=[CH:17][CH:18]=1)=[O:23])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 11116285(S)-4-methylbenzenesulfinamideHCID 579428652-[(1-Methylethyl)thio]-5-nitrobenzaldehyde

생성물 1

HCID 58789124(NE,S)-4-methyl-N-[(5-nitro-2-propan-2-ylsulfanylphenyl)methylidene]benzenesulfinamide수율 88.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
75 °C

실험 절차

To 2-(isopropylthio)-5-nitrobenzaldehyde (234 mg, 1.0 mmol) and (S)-(+)-p-toluenesulfinamide (161 mg, 1.0 mmol) in CH2Cl2 (10 mL) was added Ti(OEt)4 (25% tech, 0.54 mL). The mixture was heated at 75° C. for 3.0 h. TLC indicated a clean reaction. Solvent was removed and the residue was redissolved in EtOAc, under stirring sat. Na2SO4 solution was added and the slurry was stirred at rt for 30 min before it was filtered through a pad of Celite®. The filtrate was extracted with EtOAc, washed with brine and dried over Na2SO4. After evaporation of solvent, 98A (320 mg, 88% yield) was obtained as a solid used for next step without further purification. 1H NMR (400 MHz, CDCl3) δ ppm 1.34 (d, J=6.59 Hz, 6H) 2.34 (s, 3H) 3.51-3.61 (m, 1H) 7.27 (d, J=7.91 Hz, 2H) 7.45 (d, J=8.79 Hz, 1H) 7.59 (d, J=8.35 Hz, 2H) 8.14 (dd, J=8.79, 2.64 Hz, 1H) 8.69 (d, J=2.64 Hz, 1H) 9.17 (s, 1H).

후처리

  1. customa clean reaction
  2. customSolvent was removed
  3. dissolutionthe residue was redissolved in EtOAc, under stirring sat. Na2SO4 solution
  4. additionwas added
  5. filtrationwas filtered through a pad of Celite®
  6. extractionThe filtrate was extracted with EtOAc
  7. washwashed with brine
  8. dry with materialdried over Na2SO4
  9. customAfter evaporation of solvent

출처 및 근거

ORD 기록
ord-09d5f0f613394bbbab5bbdff444d2db2
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456195B2

반응 노트

불러오는 중…