4-Toluenesulfonyl chloride → HCID 19771312, 화합물

HRID 1589933노트

반응식

HRID 1589933 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 19771312HCID 19771312, 화합물수율 38%

시약·촉매·용매 1

HCID 180Acetone용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9f850720585b437ab1e8f7b1142c0161
출처 데이터셋
uspto-grants-1993_04
특허 번호
US05200544

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