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

HRID 236985노트

반응식

HRID 236985 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 312751,4-Dioxane용매

실험 절차

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'.

후처리

  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

출처 및 근거

ORD 기록
ord-e42a292bea5343308bccdf6f0172aa9d
출처 데이터셋
uspto-grants-1979_06
특허 번호
US04159330

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