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Ammonium Chloride → 2-(tert-Butyl-dimethyl-silyl)-5-(4-methyl-3-nitro-benzyl)-imidazole-1-sulfonic acid dimethylamide

HRID 1106744
ノート
印刷プレビュー

反応式

HRID 1106744 の反応式
[CH3:1][N:2]([CH3:18])[S:3]([N:6]1[CH2:10][CH2:9][N:8]=[C:7]1[Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])(=[O:5])=[O:4].C([Li])CCC.Br[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[C:28]([N+:33]([O-:35])=[O:34])[CH:27]=1.[Cl-].[NH4+]>O1CCCC1.CCCCCC>[CH3:1][N:2]([CH3:18])[S:3]([N:6]1[C:10]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[C:28]([N+:33]([O-:35])=[O:34])[CH:27]=2)=[CH:9][N:8]=[C:7]1[Si:11]([C:14]([CH3:15])([CH3:17])[CH3:16])([CH3:13])[CH3:12])(=[O:4])=[O:5]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 126236744-(Bromomethyl)-1-methyl-2-nitrobenzeneHCID 536506332-(tert-Butyl-dimethyl-silyl)-4,5-dihydro-imidazole-1-sulfonic acid dimethylamideHCID 178418339Butyllithium

生成物 1

HCID 539951302-(tert-Butyl-dimethyl-silyl)-5-(4-methyl-3-nitro-benzyl)-imidazole-1-sulfonic acid dimethylamide収率 31.6%

試薬・触媒・溶媒

2
HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

2-(tert-Butyl-dimethyl-silyl)-4,5-dihydro-imidazole-1-sulfonic acid dimethylamide (5.03 g) (prepared as described by Ngochindo, J. Chem. Soc. Perkin Trans. (1990) 1:1645) was dissolved in 100 ml of dry tetrahydrofuran and cooled in a dry ice-acetone bath to -78° C.; 11.9 ml of 1.6M n-butyllithium in hexane was added to this mixture. After 1 hr at -78° C., the reaction mixture was treated dropwise with 5.0 g of 4-bromomethyl-1-methyl-2-nitro-benzene dissolved in 25 ml of dry tetrahydrofuran (THF). The mixture was stirred at -78° C. for 1 hr and then allowed to come to room temperature overnight. The mixture was treated with saturated ammonium chloride, extracted with ethyl acetate washed the combined extracts with saturated sodium chloride, dried, and evaporated to dryness. The residue was purified by flash chromatography on silica gel and eluted with ethyl acetate:hexane (1:4 ) to give 2.39 g of 2-(tert-butyl-dimethyl-silyl)-5-(4-methyl-3-nitro-benzyl)-imidazole-1-sulfonic acid dimethylamide as a yellow oil. ##STR126##

後処理

  1. waitto come to room temperature overnight
  2. extractionextracted with ethyl acetate
  3. washwashed the combined extracts with saturated sodium chloride
  4. customdried
  5. customevaporated to dryness
  6. customThe residue was purified by flash chromatography on silica gel
  7. washeluted with ethyl acetate:hexane (1:4 )

出典と根拠

ORDレコード
ord-433e74c1294a4b09ac12988df54b1555
出典データセット
uspto-grants-2000_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06057349

反応ノート

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