Water → HCID 67399087、化合物

HRID 70559ノート

反応式

HRID 70559 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:13][CH2:14][OH:15])[CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:16]([Si:20]([CH3:23])([CH3:22])Cl)([CH3:19])([CH3:18])[CH3:17].C(N(CC)CC)C.O>C(Cl)(Cl)Cl.CN(C1C=CN=CC=1)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([CH2:13][CH2:14][O:15][Si:20]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:23])[CH3:22])[CH3:12])(=[O:9])=[O:10])=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 394031924-bromo-N-(2-hydroxyethyl)-N-methylbenzenesulfonamide

生成物 1

HCID 67399087HCID 67399087、化合物収率 100%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6212Chloroform溶媒

実験手順

A solution of 4-bromo-N-(2-hydroxyethyl)-N-methylbenzenesulfonamide (1.339 g) in chloroform (15 mL) was stirred in an ice bath, during which tert-butyldimethylchlorosilane (1.04 g) and N,N-dimethyl-4-aminopyridine (84 mg) were added thereto. Triethylamine were added dropwise, and the mixture was returned to room temperature and stirred for 16 hours. The reaction solution was poured into water, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5→60:40) to give 4-bromo-N-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-N-methylbenzenesulfonamide as a colorless powder (1.77 g, 100%).

後処理

  1. additionwere added
  2. customwas returned to room temperature
  3. extractionfollowed by extraction with chloroform
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5→60:40)

出典と根拠

ORDレコード
ord-bced49e2d8c64b8b8db9560ea3be668d
出典データセット
uspto-grants-2014_09
特許番号
US08822503B2

反応ノート

読み込み中…