(1,1-Dimethylethyl)urea → Ethyl 2-[(1,1-dimethylethyl)amino]-4-trifluoromethyl-5-oxazolecarboxylate

HRID 359262Notes

Reaction equation

HRID 359262 reaction equation
Cl[CH:2]([C:8]([C:10]([F:13])([F:12])[F:11])=O)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:14]([NH:18][C:19]([NH2:21])=[O:20])([CH3:17])([CH3:16])[CH3:15]>C(Cl)Cl>[CH3:15][C:14]([NH:18][C:19]1[O:20][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[C:8]([C:10]([F:13])([F:12])[F:11])[N:21]=1)([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 14233(1,1-Dimethylethyl)ureaHCID 2737165Ethyl 2-chloro-4,4,4-trifluoro-3-oxobutanoate

Product 1

HCID 20064741Ethyl 2-[(1,1-dimethylethyl)amino]-4-trifluoromethyl-5-oxazolecarboxylateYield 62.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A reaction vessel was charged with 10.9 g (50 mmol) of ethyl 2-chloro-4,4,4-trifluoroacetoacetate and 7.0 g (60 mmol) of tert-butylurea. The reaction mixture was stirred and heated at 140°-150° C. for 19 hours under a calcium sulfate drying tube. With the mixture at room temperature, the mixture was slurried in methylene chloride and washed three times with water. The methylene chloride extract was dried over magnesium sulfate and then concentrated under reduced pressure to yield 8.8 g of a mustard-colored solid material. This solid material was dissolved in hot hexane and then filtered hot. The filtrate was cooled in a dry ice bath. The filtrate yielded 7.3 g of a beige solid product (m.p.=56°-59° C.) identified in Table I.

Workup

  1. temperatureheated at 140°-150° C. for 19 hours under a calcium sulfate drying tube
  2. customat room temperature
  3. washwashed three times with water
  4. extractionThe methylene chloride extract
  5. dry with materialwas dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d5b86e1829ee4b17b6d304d59a09b9c9
Source dataset
uspto-grants-1991_03
Patent number
US05000775

Reaction notes

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