Carbamic acid, ethyl ester → HCID 53935635, compound

HRID 1757089Notes

Reaction equation

HRID 1757089 reaction equation
O=[C:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[NH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].S([O-])([O-])(=O)=O.[Na+].[Na+]>C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:16]([O:15][C:13]([NH:12][C:2]1[CH2:6][CH2:5][CH2:4][C:3]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:14])[CH3:17]

Participants

6

Reactant 3

HCID 5641Carbamic acid, ethyl esterHCID 24436Sodium SulfateHCID 69136Ethyl 2-oxocyclopentanecarboxylate

Product 1

HCID 53935635HCID 53935635, compoundYield 64.3%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolvent

Procedure

A solution containing ethyl 2-oxocyclopentanecarboxylate (90 g, 0.63 moles), urethane (63.1 g, 0.70 mole) and p-toluenesulfonic acid (1 g) in benzene (100 mL) was refluxed for 15 hours in a Soxhlet extraction apparatus with sodium sulfate in the thimble. The reaction mixture was washed with water (3×100 mL), dried over magnesium sulfate then evaporated under vacuum. The resulting residue was recrystallized from methanol:water (9:1) to provide 92.1 g of ethyl 2-[(ethoxycarbonyl)amino]-1-cyclopentene-1-carboxylate as a white solid, m.p. 49°-51° C.

Workup

  1. washThe reaction mixture was washed with water (3×100 mL)
  2. dry with materialdried over magnesium sulfate
  3. customthen evaporated under vacuum
  4. customThe resulting residue was recrystallized from methanol:water (9:1)

Sources & evidence

ORD record
ord-41fb527aba064b889a27af013e0c1f7b
Source dataset
uspto-grants-1995_08
Patent number
US05444065

Reaction notes

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