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

HRID 845971Notes

Reaction equation

HRID 845971 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].[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 521998p-Toluenesulfonic acid monohydrateSolvent

Procedure

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. This 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.

Workup

  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

Sources & evidence

ORD record
ord-e94c9234e5f543068cb4389eac858a6b
Source dataset
uspto-grants-1988_07
Patent number
US04760163

Reaction notes

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