Dimethyl 4-aminoisophthalate → Dimethyl-4-(2'-ethoxy-3'-methoxy-benzoylamino)-isophthalate

HRID 236985ノート

反応式

HRID 236985 の反応式
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[CH:12][C:11]([NH2:14])=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=1.[CH2:16]([O:18][C:19]1[C:27]([O:28][CH3:29])=[CH:26][CH:25]=[CH:24][C:20]=1[C:21](Cl)=[O:22])[CH3:17]>O1CCOCC1.N1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[CH:12][C:11]([NH:14][C:21](=[O:22])[C:20]2[CH:24]=[CH:25][CH:26]=[C:27]([O:28][CH3:29])[C:19]=2[O:18][CH2:16][CH3:17])=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=1

参加物

5

反応物 2

HCID 11095854Dimethyl 4-aminoisophthalateHCID 213147772-Ethoxy-3-methoxybenzoyl chloride

生成物 1

HCID 12528358Dimethyl-4-(2'-ethoxy-3'-methoxy-benzoylamino)-isophthalate収率 97.2%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 312751,4-Dioxane溶媒

実験手順

Dimethyl- 4-amino-isophthalate (5 g) in 50 ml of dioxane and 10 ml of anhydrous pyridine is treated with 7.5 g of 2-ethoxy-3-methoxybenzoyl chloride at room temperature, overnight. After dilution with water, the precipitate is collected, dissolved in ethyl acetate, and washed with 5% NaHCO3 and then with water. After evaporation to dryness under vacuum, the material is crystallized from isopropyl ether, yielding dimethyl- 4-(2'-ethoxy-3'-methoxy-benzoylamino)-isophthalate (9 g; m.p. 113°-115° C.), which is dissolved in 80 ml of dioxane and treated with 70 ml of 1N NaOH at room temperature for 4 hours. After acidification with diluted HCl, the precipitate is collected under vacuum and washed with water until neutral. The yield is 7.4 g of 4-(2'-ethoxy-3'-methoxy-benzoylamino)-isophthalic acid (m.p.=244°-246° C.), which are treated with 10 ml of acetic anhydride at the reflux temperature for 10'.

後処理

  1. customAfter dilution with water, the precipitate is collected
  2. dissolutiondissolved in ethyl acetate
  3. washwashed with 5% NaHCO3
  4. customAfter evaporation to dryness under vacuum
  5. customthe material is crystallized from isopropyl ether

出典と根拠

ORDレコード
ord-e42a292bea5343308bccdf6f0172aa9d
出典データセット
uspto-grants-1979_06
特許番号
US04159330

反応ノート

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