Isobutylurea → Ethyl 2-[(2-methylpropyl)amino]-4-(trifluoromethyl)-5-oxazolecarboxylate

HRID 359276Notes

Reaction equation

HRID 359276 reaction equation
[CH2:1]([NH:5][C:6]([NH2:8])=[O:7])[CH:2]([CH3:4])[CH3:3].Cl[CH:10]([C:16]([C:18]([F:21])([F:20])[F:19])=O)[C:11]([O:13][CH2:14][CH3:15])=[O:12]>>[CH3:3][CH:2]([CH3:4])[CH2:1][NH:5][C:6]1[O:7][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:16]([C:18]([F:19])([F:21])[F:20])[N:8]=1

Participants

3

Reactant 2

HCID 79051IsobutylureaHCID 2737165Ethyl 2-chloro-4,4,4-trifluoro-3-oxobutanoate

Product 1

HCID 20064723Ethyl 2-[(2-methylpropyl)amino]-4-(trifluoromethyl)-5-oxazolecarboxylateYield 33.7%

Procedure

By the procedure of Example 4, 7.0 g (60 mmol) of isobutyl urea was reacted with 10.9 g (50 mmol) of ethyl 2-chloro-4,4,4-trifluoroacetoacetate at 140°-150° C. for 18 hours. The product was separated and then recrystallized from methylcyclohexane to yield 4.72 g of a yellow powder product (m.p.=43°-44° C.) identified in Table I.

Workup

  1. customThe product was separated
  2. customrecrystallized from methylcyclohexane

Sources & evidence

ORD record
ord-14545c768b21488c861e784bf6a8acc8
Source dataset
uspto-grants-1991_03
Patent number
US05000775

Reaction notes

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