Diethyl Ether → 2-[(1,1-dimethylethyl)amino]-N-(2-hydroxy-1,1-dimethylethyl)-4-(trifluoromethyl)-5-oxazolecarboxamide

HRID 359280Notes

Reaction equation

HRID 359280 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].C(OCC)C.[C:12]([NH:16][C:17]1[O:18][C:19]([C:26](Cl)=[O:27])=[C:20]([C:22]([F:25])([F:24])[F:23])[N:21]=1)([CH3:15])([CH3:14])[CH3:13]>CCCCCC>[CH3:15][C:12]([NH:16][C:17]1[O:18][C:19]([C:26]([NH:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4])=[O:27])=[C:20]([C:22]([F:24])([F:25])[F:23])[N:21]=1)([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 3283Diethyl Ether2×HCID 118072-Amino-2-methyl-1-propanolHCID 20064749HCID 20064749, compound

Product 1

HCID 200647392-[(1,1-dimethylethyl)amino]-N-(2-hydroxy-1,1-dimethylethyl)-4-(trifluoromethyl)-5-oxazolecarboxamide

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A reaction vessel fitted with a calcium sulfate drying tube was charged with 4.9 g (55 mmol) of 2-amino-2-methyl-1-propanol and 50 ml of anhydrous ethyl ether. With this mixture stirred at 0°-5° C., there was added dropwise over a period of 45 minutes a solution of 50 ml anhydrous ethyl ether containing 6.5 g (25 mmol) of 2-(tert-butylamino)-4-trifluoromethyl-5-oxazolecarbonyl chloride. The reaction mixture was stirred at ambient temperature for 11/2 hours, then filtered to remove the HCl salt of 2-amino-2-methyl1-propanol. The ether filtrate was washed successively with one molar oxalic acid and saturated brine, then dried under magnesium sulfate, and concentrated under reduced pressure to yield 8.2 g of a colorless, viscous oil. This oil was mixed with hexane and heated to reflux to yield a white solid material. The material was cooled and filtered to yield 7.7 g of a white crystalline product (m.p.=140°-144° C.) identified in Table I.

Workup

  1. customA reaction vessel fitted with a calcium sulfate drying tube
  2. stirringThe reaction mixture was stirred at ambient temperature for 11/2 hours
  3. filtrationfiltered
  4. customto remove the HCl salt of 2-amino-2-methyl1-propanol
  5. washThe ether filtrate was washed successively with one molar oxalic acid and saturated brine
  6. customdried under magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto yield 8.2 g of a colorless, viscous oil
  9. temperatureheated
  10. temperatureto reflux
  11. customto yield a white solid material
  12. temperatureThe material was cooled
  13. filtrationfiltered

Sources & evidence

ORD record
ord-d0a82dcfd8814c90a09c4f66c3164496
Source dataset
uspto-grants-1991_03
Patent number
US05000775

Reaction notes

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