Water → Ethyl 2-chloro-5-[3-(2-ethoxycarbonyl-1-cyclopenten-1-yl)ureido]-benzoate

HRID 1252947노트

반응식

HRID 1252947 반응식
[Cl:1][C:2]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([NH2:16])=[O:15])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH3:17][CH2:18][O:19][C:20]([CH:22]1[C:26](=O)[CH2:25][CH2:24][CH2:23]1)=[O:21].O>C1C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:1][C:2]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([NH:16][C:23]2[CH2:24][CH2:25][CH2:26][C:22]=2[C:20]([O:19][CH2:18][CH3:17])=[O:21])=[O:15])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

참가 물질

6

반응물 3

HCID 962WaterHCID 69136Ethyl 2-oxocyclopentanecarboxylateHCID 21270735Ethyl 2-chloro-5-ureidobenzoate

생성물 1

HCID 21270704Ethyl 2-chloro-5-[3-(2-ethoxycarbonyl-1-cyclopenten-1-yl)ureido]-benzoate

시약·촉매·용매 2

HCID 241Benzene용매HCID 521998p-Toluenesulfonic acid monohydrate용매

실험 절차

48.4 g of ethyl 2-chloro-5-ureido-benzoate and 31.2 g of ethyl cyclopentanone-2-carboxylate are heated under reflux for 6 hours in 500 ml of benzene and 2 g of toluene-4-sulphonic acid monohydrate. The water formed is removed by means of a water separator. The reaction mixture is subsequently evaporated to dryness, the residue is dissolved in 700 ml of diethyl ether and the solution is filtered. The filtrate is evaporated to dryness and the residue is purified by chromatography on 1.5 g of silica gel using diethyl ether/n-hexane (1:2) as the eluent. There is obtained ethyl 2-chloro-5-{3-[2-(ethoxycarbonyl)-1-cyclopenten-1-yl]ureido}-benzoate as colourless crystals. The product is recrystallized from diethyl ether/n-hexane, m.p. 110°-112° C.

후처리

  1. customis removed by means of a water separator
  2. customThe reaction mixture is subsequently evaporated to dryness
  3. dissolutionthe residue is dissolved in 700 ml of diethyl ether
  4. filtrationthe solution is filtered
  5. customThe filtrate is evaporated to dryness
  6. customthe residue is purified by chromatography on 1.5 g of silica gel

출처 및 근거

ORD 기록
ord-d62dbbf4fce5490495a44deb652a1830
출처 데이터셋
uspto-grants-1988_05
특허 번호
US04746352

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