4-Toluenesulfonyl chloride → HCID 19771312、化合物

HRID 1589933ノート

反応式

HRID 1589933 の反応式
[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:3]=1[CH2:4][OH:5].[S:13](Cl)([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)(=[O:15])=[O:14].C1(NC2CCCCC2)CCCCC1>CC(C)=O>[S:13]([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)([O:5][CH2:4][C:3]1[C:6]([N+:10]([O-:12])=[O:11])=[CH:7][CH:8]=[CH:9][C:2]=1[CH3:1])(=[O:15])=[O:14]

参加物

5

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 7582DicyclohexylamineHCID 12204069(2-Methyl-6-nitrophenyl)methanol

生成物 1

HCID 19771312HCID 19771312、化合物収率 38%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒2 回

実験手順

A 100 mL round bottomed flask equipped with a dropping funnel was charged with 2.50 g of 2-methyl-6-nitrobenzyl alcohol and 3.14 g of tosyl chloride dissolved in 30 mL of dry acetone under argon. To the mixture was added dropwise 3.30 mL of dicyclohexylamine dissolved in 5 mL of dry acetone while cooling so as to keep the temperature below 15° C. The reaction mixture was brought to room temperature and stirred for 1 day. The mixture was filtered to remove dicyclohexylamine hydrochloride, the solvent removed under vacuum, and the residue chromatographed over silica gel using carbon tetrachloride as the eluent. The product was recrystallized from methylene chloride/pentane to give 1.82 g (38% yield) of white crystals.

後処理

  1. customA 100 mL round bottomed flask equipped with a dropping funnel
  2. temperaturewhile cooling so as
  3. customthe temperature below 15° C
  4. customwas brought to room temperature
  5. filtrationThe mixture was filtered
  6. customto remove dicyclohexylamine hydrochloride
  7. customthe solvent removed under vacuum
  8. customthe residue chromatographed over silica gel
  9. customThe product was recrystallized from methylene chloride/pentane

出典と根拠

ORDレコード
ord-9f850720585b437ab1e8f7b1142c0161
出典データセット
uspto-grants-1993_04
特許番号
US05200544

反応ノート

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