Iodoethane → N-ethyl-2,6-dimethoxy-4-(methoxy-carbonyl)carbanilic acid benzyl ester

HRID 414542ノート

反応式

HRID 414542 の反応式
[CH2:1]([O:8][C:9](=[O:25])[NH:10][C:11]1[C:16]([O:17][CH3:18])=[CH:15][C:14]([C:19]([O:21][CH3:22])=[O:20])=[CH:13][C:12]=1[O:23][CH3:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:28](I)[CH3:29]>CN(C)C=O>[CH2:1]([O:8][C:9](=[O:25])[N:10]([CH2:28][CH3:29])[C:11]1[C:12]([O:23][CH3:24])=[CH:13][C:14]([C:19]([O:21][CH3:22])=[O:20])=[CH:15][C:16]=1[O:17][CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 542260132,6-Dimethoxy-4-(methoxy-carbonyl)-carbanilic acid benzyl ester

生成物 1

HCID 53836153N-ethyl-2,6-dimethoxy-4-(methoxy-carbonyl)carbanilic acid benzyl ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A suspension of 103 g. of 2,6-dimethoxy-4-(methoxy-carbonyl)-carbanilic acid benzyl ester and 17.3 g. of sodium hydride (50% dispersion in oil) in 1 liter of absolute dimethylformamide was stirred at room temperature for 4 hours and subsequently treated with 56.2 g. of ethyl iodide with stirring and ice-cooling. After stirring at room temperature for 30 minutes, the dimethylformamide was removed at 60° C. under vacuum. Then, 1 liter of water was added to the residue and the mixture was extracted with two 1.5 liter portions of ethyl acetate. The ethyl acetate extract was washed with two 700 ml. portions of water, dried over magnesium sulfate and evaporated under vacuum. After recrystallization of the residue from alcohol, there was obtained N-ethyl-2,6-dimethoxy-4-(methoxy-carbonyl)-carbanilic acid benzyl ester having a melting point of 85°-86° C.

後処理

  1. additionA suspension of 103 g
  2. additionsubsequently treated with 56.2 g
  3. temperatureice-cooling
  4. customthe dimethylformamide was removed at 60° C. under vacuum
  5. additionThen, 1 liter of water was added to the residue
  6. extractionthe mixture was extracted with two 1.5 liter portions of ethyl acetate
  7. extractionThe ethyl acetate extract
  8. washwas washed with two 700 ml
  9. dry with materialportions of water, dried over magnesium sulfate
  10. customevaporated under vacuum
  11. customAfter recrystallization of the residue from alcohol

出典と根拠

ORDレコード
ord-68a83aa754e64e7bbadcb38e49d7e975
出典データセット
uspto-grants-1988_12
特許番号
US04792557

反応ノート

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