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1,4-Dibromobutane → N-[4-(4-Bromo-butoxy)-phenyl]-N-methyl-4-trifluoromethyl-benzenesulfonamide

HRID 1841597
ノート
印刷プレビュー

反応式

HRID 1841597 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:22])[S:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:4][CH:3]=1.[Br:23][CH2:24][CH2:25][CH2:26][CH2:27]Br.[H-].[Na+].[NH4+].[Cl-]>CN(C=O)C>[Br:23][CH2:24][CH2:25][CH2:26][CH2:27][O:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:22])[S:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:19])[F:20])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 80561,4-DibromobutaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 23446603N-(4-hydroxy-phenyl)-N-methyl-4-trifluoromethyl-benzenesulfonamide

生成物 1

HCID 23446540N-[4-(4-Bromo-butoxy)-phenyl]-N-methyl-4-trifluoromethyl-benzenesulfonamide収率 83%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

A solution of 6.63 g (20 mmol) of N-(4-Hydroxy-phenyl)-N-methyl-4-trifluoromethyl-benzenesulfonamide in 150 ml of DMF was treated with 7.1 ml (60 mmol) of 1,4-dibromobutane and with 1.00 g (23 mmol) of 55% NaH (in small portions) at 0° C. The reaction mixture was stirred for 4 h at RT, poured into cooled aqueous saturated NH4Cl and extracted (Et2O 3×). The organic phase was washed with aqueous 10% NaCl, dried (NaSO4) evaporated and purified by flash silica gel column (first with hexane to remove the dibromobutane and then Hexane/EtOAc 95:5) to yield 7.7 g (83%) of N-[4-(4-Bromo-butoxy)-phenyl]-N-methyl-4-trifluoromethyl-benzenesulfonamide, mp: 91-92° C.; MS: 465 (M, 1 Br).

後処理

  1. additionpoured
  2. extractionextracted (Et2O 3×)
  3. washThe organic phase was washed with aqueous 10% NaCl
  4. dry with materialdried (NaSO4)
  5. customevaporated
  6. custompurified by flash silica gel column (first with hexane
  7. customto remove the dibromobutane

出典と根拠

ORDレコード
ord-32f9a48d56e748fd9a9e7d04fca22d57
出典データセット
uspto-grants-2004_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06683201B2

反応ノート

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