Toluene → 2-Bromo-N-(3-methoxyphenyl)-N-methyl-propanamide

HRID 1767

反応式

HRID 1767 の反応式
[CH3:1][NH:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[O:6][CH3:7].C(N(CC)CC)C.C1(C)C=CC=CC=1.[Br:25][CH:26]([CH3:30])[C:27](Br)=[O:28]>O>[Br:25][CH:26]([CH3:30])[C:27]([N:2]([C:3]1[CH:10]=[CH:9][CH:8]=[C:5]([O:6][CH3:7])[CH:4]=1)[CH3:1])=[O:28]

参加物

6

反応物 4

HCID 1140TolueneHCID 8471TriethylamineHCID 79047Propanoyl bromide, 2-bromo-HCID 84349N-Methyl-m-anisidine

生成物 1

HCID 196929362-Bromo-N-(3-methoxyphenyl)-N-methyl-propanamide

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A solution of N-methyl-m-anisidine (265 g), triethylamine (269 ml) and toluene (550 ml) was stirred at 0° C. as 2-bromopropionyl bromide (202.6 ml) was added dropwise. The mixture was mechanically stirred overnight at room temperature. Water was added to the reaction and the aqueous layer was collected and extracted with ethyl acetate. All organic phases were combined, washed with 2N HCl, and dried (Na2SO4). The solvent was evaporated to yield an oil which was purified using Kugelrohr distillation. The distillate was dissolved in isopropyl ether. The solid product, 2-Bromo-N-(3-methoxyphenyl)-N-methyl-propanamide, m.p. 55°-56° C., crystallized from this solution.

後処理

  1. additionwas added dropwise
  2. customthe aqueous layer was collected
  3. extractionextracted with ethyl acetate
  4. washwashed with 2N HCl
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was evaporated
  7. customto yield an oil which
  8. customwas purified
  9. distillationKugelrohr distillation
  10. dissolutionThe distillate was dissolved in isopropyl ether
  11. customThe solid product, 2-Bromo-N-(3-methoxyphenyl)-N-methyl-propanamide, m.p. 55°-56° C., crystallized from this solution

出典と根拠

ORDレコード
ord-8b32fa3382184901ae70790edf4034ba
出典データセット
uspto-grants-1998_03
特許番号
US05726323

関連ノート

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