Toluene → Ethyl 2-[(2-ethoxy-2-oxoethyl)amino]-4-(trifluoromethyl)-5-oxazolecarboxylate

HRID 359272Notes

Reaction equation

HRID 359272 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH2:7])[CH3:3].C1(C)C=CC=CC=1.Cl[C:17]1[O:18][C:19]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:20]([C:22]([F:25])([F:24])[F:23])[N:21]=1.C(N(CC)CC)C>>[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH:7][C:17]1[O:18][C:19]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:20]([C:22]([F:24])([F:23])[F:25])[N:21]=1)[CH3:3]

Participants

5

Reactant 4

HCID 1140TolueneHCID 8471TriethylamineHCID 2723640Glycine ethyl ester, hydrochlorideHCID 12785855Ethyl 2-chloro-4-(trifluoromethyl)oxazole-5-carboxylate

Product 1

HCID 20064722Ethyl 2-[(2-ethoxy-2-oxoethyl)amino]-4-(trifluoromethyl)-5-oxazolecarboxylate

Procedure

By the procedure of Example 15, 4.19 g (0.03 mol) of glycine ethyl ester hydrochloride was added to a mixture of 100 ml toluene containing 4.87 g (0.02 mol) of ethyl 2-chloro-4-trifluoromethyl-5-oxazolecarboxylate and 6.07 g (0.06 mol) of triethylamine. The reaction mixture was stirred at ambient temperature for 48 hours. The product was separated and then recrystallized from methylcyclohexane to yield 3.55 g of a yellow powder product (m.p.=62°-63° C.) identified in Table I.

Workup

  1. customThe product was separated
  2. customrecrystallized from methylcyclohexane

Sources & evidence

ORD record
ord-503f82248de248f6825605edc8769b29
Source dataset
uspto-grants-1991_03
Patent number
US05000775

Reaction notes

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