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

HRID 2212182

반응식

HRID 2212182 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-038dd8b7cf0c49c0919656a02eb5a167
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07101891B2

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