Isopropylurea → Ethyl 2-[(1-methylethyl)amino]-4-(trifluoromethyl)-5-oxazolecarboxylate

HRID 359267Notes

Reaction equation

HRID 359267 reaction equation
[CH:1]([NH:4][C:5]([NH2:7])=[O:6])([CH3:3])[CH3:2].Cl[CH:9]([C:15]([C:17]([F:20])([F:19])[F:18])=O)[C:10]([O:12][CH2:13][CH3:14])=[O:11]>C(Cl)Cl>[CH3:2][CH:1]([NH:4][C:5]1[O:6][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:15]([C:17]([F:18])([F:20])[F:19])[N:7]=1)[CH3:3]

Participants

4

Reactant 2

HCID 12725IsopropylureaHCID 2737165Ethyl 2-chloro-4,4,4-trifluoro-3-oxobutanoate

Product 1

HCID 20064762Ethyl 2-[(1-methylethyl)amino]-4-(trifluoromethyl)-5-oxazolecarboxylateYield 47.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

By the procedure of Example 4, 6.1 g (60 mmol) of isopropyl urea was reacted with 10.9 g (50 mmol) 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 6.3 g of crystal product (m.p.=51°-52° 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-9ef2e699f2394a58a3ff5ee84044443e
Source dataset
uspto-grants-1991_03
Patent number
US05000775

Reaction notes

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