Ethyl 2-chloroacetoacetate → Ethyl 2-(cyclopentylamino)-4-methyl-5-oxazolecarboxylate

HRID 359293Notes

Reaction equation

HRID 359293 reaction equation
[CH:1]1([NH:6][C:7]([NH2:9])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH:11]([C:17]([CH3:19])=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13]>>[CH:1]1([NH:6][C:7]2[O:8][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:17]([CH3:19])[N:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 294526Cyclopentylurea

Product 1

HCID 20064778Ethyl 2-(cyclopentylamino)-4-methyl-5-oxazolecarboxylateYield 16.4%

Procedure

By the procedure of Example 4, 10 g (78 mmol) of cyclopentyl urea was reacted with 10.7 g (65 mmol) of ethyl 2-chloroacetoacetate at 140°-150° C. for 4 hours. The product was separated, then purified by Kugelrohr distillation (135° C. @ 0.5 mm Hg) and then recrystallized from hexane to yield 2.54 g of a light yellow solid product (m.p.=50°-52° C.) identified in Table I.

Workup

  1. customThe product was separated
  2. distillationpurified by Kugelrohr distillation (135° C. @ 0.5 mm Hg)
  3. customrecrystallized from hexane

Sources & evidence

ORD record
ord-86b47fb6624944888b8827e580124042
Source dataset
uspto-grants-1991_03
Patent number
US05000775

Reaction notes

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