Hydrochloric Acid → HCID 15812073, compound

HRID 359278Notes

Reaction equation

HRID 359278 reaction equation
O1CCCC1.[CH3:6][C:7]([NH:10][C:11]1[O:12][C:13]([C:20]([O:22]CC)=[O:21])=[C:14]([C:16]([F:19])([F:18])[F:17])[N:15]=1)([CH3:9])[CH3:8].[OH-].[Na+].Cl>O>[CH3:9][C:7]([NH:10][C:11]1[O:12][C:13]([C:20]([OH:22])=[O:21])=[C:14]([C:16]([F:17])([F:19])[F:18])[N:15]=1)([CH3:6])[CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 20064741Ethyl 2-[(1,1-dimethylethyl)amino]-4-trifluoromethyl-5-oxazolecarboxylate

Product 1

HCID 15812073HCID 15812073, compoundYield 9.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A reaction vessel was charged with 200 ml tetrahydrofuran and 28 g (100 mmol) of ethyl 2-[(1,1dimethylethyl)amino]-4-trifluoromethyl-5-oxazolecarboxylate (prepared by Example 6). With this mixture stirred at ambient temperature, 50% aqueous sodium hydroxide (16 g; 200 mmol) was added followed by 50 ml water as a rinse. The reaction mixture was stirred at ambient temperature for 16 hours. The mixture was then poured into 500 ml of 5% hydrochloric acid. After cooling with an ice bath, the mixture was filtered, washed with water, and then dried to yield 2.4 g of a white powder which was recrystallized from ethyl acetate to a crystalline product (m.p.=256°-258° C.) identified in Table I.

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for 16 hours
  2. temperatureAfter cooling with an ice bath
  3. filtrationthe mixture was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-25e059f518784467abbaad415a2e5cf5
Source dataset
uspto-grants-1991_03
Patent number
US05000775

Reaction notes

Loading…