Dimethyl Sulfate → 4-Methoxy-N-methyl-3-nitrobenzeneacetamide

HRID 975927ノート

反応式

HRID 975927 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][CH3:12])=[O:10])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[C:16](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O.S([O-])(OC)(=O)=O>CN(C=O)C.O>[CH3:16][O:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][CH3:12])=[O:10])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14]

参加物

7

反応物 4

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 4694097Methyl sulfate(1-)HCID 134095334-hydroxy-N-methyl-3-nitrobenzeneacetamide

生成物 1

HCID 134095344-Methoxy-N-methyl-3-nitrobenzeneacetamide収率 82%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 4.2 g (19.8 mmol) of 4-hydroxy-N-methyl-3 -nitrobenzeneacetamide in 50 mL of DMF containing 5.5 g of anhydrous potassium carbonate was added 5.6 mL of dimethyl sulfate. The mixture was heated at 60°-70° C. for 45 min, treated with an additional 3.0 mL of methyl sulfate, and heated for another 30 min. The mixture was cooled, poured into 200 mL water, and extracted with dichloromethane. The extracts were washed with water, dried and evaporated to give a solid which was recrystallized from ethanol-water to afford 3.7 g of a yellowish solid (82%). 1H NMR (300 MHz, CDCl3) δ 7.71 (s, 1H), 7.47 (d, 1H, J =9.0 Hz), 7.25 (d, 1H, J =8.4 Hz), 5.71 (brs, 1H), 3.90 (s, 3H) 3.47 (s, 2H), 2.75 (d, 3H, J=4.8 Hz).

後処理

  1. temperatureThe mixture was heated at 60°-70° C. for 45 min
  2. temperatureheated for another 30 min
  3. temperatureThe mixture was cooled
  4. extractionextracted with dichloromethane
  5. washThe extracts were washed with water
  6. customdried
  7. customevaporated
  8. customto give a solid which
  9. customwas recrystallized from ethanol-water

出典と根拠

ORDレコード
ord-9296010060b6485aba8463c6a3b5e3eb
出典データセット
uspto-grants-1997_03
特許番号
US05610174

反応ノート

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