Phenylurea → Ethyl 2-(phenylamino)4(trifluoromethyl)-5-oxazolecarboxylate

HRID 359268

Reaction equation

HRID 359268 reaction equation
[C:1]1([NH:7][C:8]([NH2:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH:12]([C:18]([C:20]([F:23])([F:22])[F:21])=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14]>C(Cl)Cl>[C:1]1([NH:7][C:8]2[O:9][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:18]([C:20]([F:21])([F:23])[F:22])[N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6145PhenylureaHCID 2737165Ethyl 2-chloro-4,4,4-trifluoro-3-oxobutanoate

Product 1

HCID 20064757Ethyl 2-(phenylamino)4(trifluoromethyl)-5-oxazolecarboxylateYield 41.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

By the procedure of Example 4, 8.2 g (60 mmol) of phenyl urea was reacted with 10.9 g (50 mmol) of ethyl 2-chloro-4,4,4-trifluoroacetoacetate at 140°-150° C. for 24 hours. The product mixture was treated with methylene chloride, washed with water, dried and concentrated. The residue was recrystallized from methylcyclohexane to yield 6.2 g of crystal product (m.p.=114°-116° C.) identified in Table I.

Workup

  1. washwashed with water
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was recrystallized from methylcyclohexane

Sources & evidence

ORD record
ord-3b385644b6ea42398ac5304fb80aadc0
Source dataset
uspto-grants-1991_03
Patent number
US05000775

Linked notes

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