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

HRID 272784ノート

反応式

HRID 272784 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
75 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-09d5f0f613394bbbab5bbdff444d2db2
出典データセット
uspto-grants-2008_11
特許番号
US07456195B2

反応ノート

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