Triethylamine → 2-Bromo-N-(3,4,5-trimethoxy-phenyl)-acetamide

HRID 2212182

反応式

HRID 2212182 の反応式
C(N(CC)CC)C.[Br:8][CH2:9][C:10](Br)=[O:11].[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:19]=[C:20]([O:24][CH3:25])[C:21]=1[O:22][CH3:23])[NH2:18]>O1CCCC1>[Br:8][CH2:9][C:10]([NH:18][C:17]1[CH:19]=[C:20]([O:24][CH3:25])[C:21]([O:22][CH3:23])=[C:15]([O:14][CH3:13])[CH:16]=1)=[O:11]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 322853,4,5-TrimethoxyanilineHCID 61147Bromoacetyl bromide

生成物 1

HCID 219637112-Bromo-N-(3,4,5-trimethoxy-phenyl)-acetamide収率 87%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Add triethylamine (1.53 mL, 11.0 mmol) and bromoacetyl bromide (0.87 mL, 10.0 mmol) dropwise to a 0° C. solution of 3,4,5-trimethoxy-aniline (1.74 g, 9.5 mmol) in tetrahydrofuran (30 mL). Allow the reaction to warm to room temperature overnight. Filter the mixture, wash with tetrahydrofuran, and concentrate. Dissolve the resulting brown solid in chloroform; wash with 1N HCl, saturated aqueous sodium bicarbonate solution, and brine; dry over magnesium sulfate; and concentrate. Purify by flash chromatography on silica gel (eluting with 0–1% methanol/chloroform) to give 2.50 g of the title compound as an orange solid, 87% yield. 1H NMR: consistent with structure. MS (ion spray) 304 (M+).

後処理

  1. customthe reaction
  2. filtrationFilter the mixture
  3. washwash with tetrahydrofuran
  4. concentrationconcentrate
  5. dissolutionDissolve the resulting brown solid in chloroform
  6. washwash with 1N HCl, saturated aqueous sodium bicarbonate solution, and brine
  7. dry with materialdry over magnesium sulfate
  8. concentrationand concentrate
  9. customPurify by flash chromatography on silica gel (eluting with 0–1% methanol/chloroform)

出典と根拠

ORDレコード
ord-038dd8b7cf0c49c0919656a02eb5a167
出典データセット
uspto-grants-2006_09
特許番号
US07101891B2

関連ノート

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