Ethyl 2-oxocyclopentanecarboxylate → HCID 20026019, compound

HRID 1722936Notes

Reaction equation

HRID 1722936 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:6][C:5]([NH:12][C:13]([NH2:15])=[O:14])=[C:4]([F:16])[CH:3]=1.[CH3:17][CH2:18][O:19][C:20]([CH:22]1[C:26](=O)[CH2:25][CH2:24][CH2:23]1)=[O:21].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[Cl:1][C:2]1[C:7]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:6][C:5]([NH:12][C:13](=[O:14])[NH:15][C:23]2[CH2:24][CH2:25][CH2:26][C:22]=2[C:20]([O:19][CH2:18][CH3:17])=[O:21])=[C:4]([F:16])[CH:3]=1

Participants

5

Reactant 3

HCID 69136Ethyl 2-oxocyclopentanecarboxylateHCID 521998p-Toluenesulfonic acid monohydrateHCID 177702854-Chloro-2-fluoro-5-isopropoxyphenylurea

Product 1

HCID 20026019HCID 20026019, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

7.00 g of 4-chloro-2-fluoro-5-isopropoxyphenylurea and 4.44 g of ethyl cyclopentanone-2-carboxylate are heated at reflux temperature for 1.5 hours with 0.3 g of toluene-4-sulphonic acid monohydrate in 150 ml of benzene. The water which forms is removed with a water separator. The reaction mixture is subsequently evaporated to dryness and the residue is purified by chromatography on a silica gel column using methylene chloride as the eluent and recrystallized from diethyl ether/n-hexane. There is obtained ethyl 2-[3-(4-chloro-2-fluoro-5 -isopropoxyphenyl)-ureido]-1-cyclopentenecarboxylate, m.p. 166°-169° C.

Workup

  1. customThe water which forms is removed with a water separator
  2. customThe reaction mixture is subsequently evaporated to dryness
  3. customthe residue is purified by chromatography on a silica gel column
  4. customrecrystallized from diethyl ether/n-hexane

Sources & evidence

ORD record
ord-45e58f077d884d689f7fe6f26c9dd699
Source dataset
uspto-grants-1989_08
Patent number
US04859229

Reaction notes

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