Acetic Acid → ethyl 2-chloro-5-(1,2,4,5,6,7-hexahydro-2,4-dioxo-3H-cyclopenta[d]pyrimidin-3-yl)-benzoate

HRID 845902Notes

Reaction equation

HRID 845902 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([NH:16][C:17]2[CH2:21][CH2:20][CH2:19][C:18]=2[C:22]([O:24]CC)=O)=[O:15])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[H-].[Na+].C(O)(=O)C>COCCOC>[Cl:1][C:2]1[CH:12]=[CH:11][C:10]([N:13]2[C:22](=[O:24])[C:18]3[CH2:19][CH2:20][CH2:21][C:17]=3[NH:16][C:14]2=[O:15])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 21270704Ethyl 2-chloro-5-[3-(2-ethoxycarbonyl-1-cyclopenten-1-yl)ureido]-benzoate

Product 1

HCID 21270732ethyl 2-chloro-5-(1,2,4,5,6,7-hexahydro-2,4-dioxo-3H-cyclopenta[d]pyrimidin-3-yl)-benzoate

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

A solution of 118.0 g of ethyl 2-chloro-5-{3-[2-(ethoxycarbonyl)-1-cyclopenten-1-yl]ureido}-benzoate in 800 ml of absolute 1,2-dimethoxyethane, is added dropwise while stirring at 20° C. during 10 minutes to a suspension of 7.7 g of sodium hydride in 800 ml of absolute 1,2-dimethoxyethane. The reaction mixture is subsequently stirred for 1 hour, treated with 20 ml of acetic acid and evaporated to dryness under reduced pressure. The residue is dissolved in 2 l of methylene chloride and washed twice with 1 l of water. The organic phase is dried over anhydrous sodium sulphate and evaporated up to crystallization. The residue is treated with 1 l of n-hexane and the crystals are filtered off under suction and rinsed with n-hexane. There is obtained ethyl 2-chloro-5-(1,2,4,5,6,7-hexahydro-2,4-dioxo-3H-cyclopenta[d]pyrimidin-3-yl)-benzoate, m.p. 178°-180° C.

Workup

  1. customevaporated to dryness under reduced pressure
  2. dissolutionThe residue is dissolved in 2 l of methylene chloride
  3. washwashed twice with 1 l of water
  4. dry with materialThe organic phase is dried over anhydrous sodium sulphate
  5. customevaporated up to crystallization
  6. additionThe residue is treated with 1 l of n-hexane
  7. filtrationthe crystals are filtered off under suction
  8. washrinsed with n-hexane

Sources & evidence

ORD record
ord-2374e5e68c774becb4c9daccb1cb6d5b
Source dataset
uspto-grants-1988_07
Patent number
US04760163

Reaction notes

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