Hydrochloric Acid → Ethyl 2-chloro-5-{3-[2-(ethoxycarbonyl)vinyl]ureido}-benzoate

HRID 1252969

Reaction equation

HRID 1252969 reaction equation
[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].C(O[CH:20]=[CH:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])C.Cl>COCCOC>[Cl:1][C:2]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([NH:16][CH:20]=[CH:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:15])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 221780Ethyl 3-ethoxy-2-propenoateHCID 21270735Ethyl 2-chloro-5-ureidobenzoate

Product 1

HCID 54346642Ethyl 2-chloro-5-{3-[2-(ethoxycarbonyl)vinyl]ureido}-benzoate

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

6.0 g of ethyl 2-chloro-5-ureidobenzoate and 6.4 g of ethyl 3-ethoxyacrylate are heated at reflux temperature in 100 ml of 1,2-dimethoxyethane and subsequently heated at this temperature with 12 ml of 2N hydrochloric acid for 5 minutes. The reaction mixture is evaporated to dryness under reduced pressure and the residue is purified by chromatography on 300 g of silica gel using ethyl acetate/n-hexane (1:3) as the eluent. There is obtained ethyl 2-chloro-5-{3-[2-(ethoxycarbonyl)vinyl]ureido}-benzoate, m.p. 116°-117° C.

Workup

  1. customThe reaction mixture is evaporated to dryness under reduced pressure
  2. customthe residue is purified by chromatography on 300 g of silica gel

Sources & evidence

ORD record
ord-44d22b3f272f45bc8bd880d0d851fd2a
Source dataset
uspto-grants-1988_05
Patent number
US04746352

Linked notes

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