Methyl 4-aminobenzoate → Methyl 4-[3-(1-adamantyl)-4-methoxybenzylideneamino]benzoate

HRID 1290598ノート

反応式

HRID 1290598 の反応式
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[C:12]12([C:22]3[CH:23]=[C:24]([CH:27]=[CH:28][C:29]=3[O:30][CH3:31])[CH:25]=O)[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]3)[CH2:13]1)[CH2:19]2>ClCCl>[C:12]12([C:22]3[CH:23]=[C:24]([CH:27]=[CH:28][C:29]=3[O:30][CH3:31])[CH:25]=[N:1][C:2]3[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=3)[CH2:13][CH:14]3[CH2:15][CH:16]([CH2:17][CH:18]([CH2:20]3)[CH2:19]1)[CH2:21]2

参加物

4

反応物 2

HCID 12082Methyl 4-aminobenzoateHCID 540295304-Methoxy-3-tricyclo[3.3.1.13,7]dec-1-ylbenzaldehyde

生成物 1

HCID 67591566Methyl 4-[3-(1-adamantyl)-4-methoxybenzylideneamino]benzoate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

3 g of basic alumina and 1.94 g (12.9 mmoles) of methyl 4-aminobenzoate are mixed in a mortar, then introduced into a round bottom flask. 3 g (11.1 mmoles) of 3-(1-adamantyl)-4-methoxybenzaldehyde in 50 ml of anhydrous dichloromethane are added with stirring. After heating at reflux for 24 hours, the reaction medium is extracted with dichloromethane and evaporated to dryness. The crude product is recrystallized in a mixture of ethyl acetate and acetone. After filtration, 3.4 g (75%) of the expected product whose melting point is 180°-182° C. are obtained.

後処理

  1. additionintroduced into a round bottom flask
  2. temperatureAfter heating
  3. temperatureat reflux for 24 hours
  4. extractionthe reaction medium is extracted with dichloromethane
  5. customevaporated to dryness
  6. customThe crude product is recrystallized in a mixture of ethyl acetate and acetone
  7. filtrationAfter filtration, 3.4 g (75%) of the expected product whose melting point is 180°-182° C.
  8. customare obtained

出典と根拠

ORDレコード
ord-d9577ea974d04a0585e3319f112d4521
出典データセット
uspto-grants-1998_05
特許番号
US05753239

反応ノート

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