Hydrochloric Acid → Bis(4-n-butylcyclohexylsulfonyl)diazomethane

HRID 51189

反応式

HRID 51189 の反応式
[CH2:1]([CH:5]1[CH2:10][CH2:9][CH:8]([S:11]([CH2:14][S:15]([CH:18]2[CH2:23][CH2:22][CH:21]([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:19]2)(=[O:17])=[O:16])(=[O:13])=[O:12])[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].C1(C)C=CC(S([N:37]=[N+:38]=[N-])(=O)=O)=CC=1.O.Cl>ClCCl>[CH2:1]([CH:5]1[CH2:6][CH2:7][CH:8]([S:11]([C:14]([S:15]([CH:18]2[CH2:23][CH2:22][CH:21]([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:19]2)(=[O:17])=[O:16])=[N+:37]=[N-:38])(=[O:13])=[O:12])[CH2:9][CH2:10]1)[CH2:2][CH2:3][CH3:4]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 13661p-Toluenesulfonyl azideHCID 22737628Bis(4-n-butylcyclohexylsulfonyl)methane

生成物 1

HCID 22737649Bis(4-n-butylcyclohexylsulfonyl)diazomethane収率 20.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

In 91 g of dichloromethane were dissolved 10.5 g (0.025 mol) of the bis(4-n-butylcyclohexylsulfonyl)methane prepared above and 7.5 g (0.038 mol) of p-toluenesulfonylazide. The solution was cooled on an ice bath, to which 3.7 ml (0.0025 mol) of diazabicyclo[5.4.0]-7-undecene (DBU) was added dropwise at a temperature below 5° C. The solution was ripened at the temperature for 15 minutes, after which 38 g of water and 10 g of 12N conc. hydrochloric acid were added. The organic layer was separated and washed with 50 g of water. The solvent was distilled off in vacuum, leaving an oily matter. It was purified by silica gel column chromatography (using dichloromethane as a developing solvent), obtaining 2.3 g of the desired bis(4-n-butylcyclohexylsulfonyl)diazomethane. The yield was 20%.

後処理

  1. additionwas added dropwise at a temperature below 5° C
  2. customThe organic layer was separated
  3. washwashed with 50 g of water
  4. distillationThe solvent was distilled off in vacuum
  5. customleaving an oily matter
  6. customIt was purified by silica gel column chromatography (

出典と根拠

ORDレコード
ord-710f2b20ca6b4f8b8c10f43115d88589
出典データセット
uspto-grants-2004_03
特許番号
US06713612B2

関連ノート

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