p-Toluenesulfonic acid monohydrate → Isopropyl 2-chloro-4-fluoro-5-{3-[2-(methoxycarbonyl)propenyl]ureido}-benzoate

HRID 845994노트

반응식

HRID 845994 반응식
[Cl:1][C:2]1[CH:13]=[C:12]([F:14])[C:11]([NH:15][C:16]([NH2:18])=[O:17])=[CH:10][C:3]=1[C:4]([O:6][CH:7]([CH3:9])[CH3:8])=[O:5].CO[CH:21]=[C:22]([CH3:27])[C:23]([O:25][CH3:26])=[O:24].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[Cl:1][C:2]1[CH:13]=[C:12]([F:14])[C:11]([NH:15][C:16]([NH:18][CH:21]=[C:22]([C:23]([O:25][CH3:26])=[O:24])[CH3:27])=[O:17])=[CH:10][C:3]=1[C:4]([O:6][CH:7]([CH3:9])[CH3:8])=[O:5]

참가 물질

5

반응물 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 3019052Methyl 3-methoxy-2-methyl-acrylateHCID 20130672Isopropyl 2-chloro-4-fluoro-5-ureidobenzoate

생성물 1

HCID 54564066Isopropyl 2-chloro-4-fluoro-5-{3-[2-(methoxycarbonyl)propenyl]ureido}-benzoate

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

27.4 g of isopropyl 2-chloro-4-fluoro-5-ureidobenzoate and 13.0 g of methyl 3-methoxy-2-methyl-acrylate are heated under reflux for 2 hours in 250 ml of benzene with 1.9 g of toluene-4-sulphonic acid monohydrate. The reaction mixture is evaporated to dryness under reduced pressure and the residue is stirred with 400 ml of diethyl ether. The insoluble material is filtered off under suction and the filtrate is evaporated to dryness under reduced pressure. The residue is purified by chromatography on 1 kg of silica gel using ethyl acetate/n-hexane (1:3) as the eluent. There is obtained isopropyl 2-chloro-4-fluoro-5-{3-[2-(methoxycarbonyl)propenyl]ureido}-benzoate, m.p. 189°-190° C.

후처리

  1. customThe reaction mixture is evaporated to dryness under reduced pressure
  2. filtrationThe insoluble material is filtered off under suction
  3. customthe filtrate is evaporated to dryness under reduced pressure
  4. customThe residue is purified by chromatography on 1 kg of silica gel

출처 및 근거

ORD 기록
ord-1b7786e7d43c4426bc5186fa683b7598
출처 데이터셋
uspto-grants-1988_07
특허 번호
US04760163

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