Hydrochloric Acid → 5-[4-(Trifluoromethyl)phenyl]-1,2-oxazol-3-amine

HRID 1156524Notes

Reaction equation

HRID 1156524 reaction equation
COC=CC#[N:6].[F:7][C:8]([F:24])([F:23])[C:9]1[CH:14]=[CH:13][C:12]([C:15]([O:21]C)(OC)[CH2:16][C:17]#[N:18])=[CH:11][CH:10]=1.NO.Cl.C[O-].[Na+]>CO>[F:7][C:8]([F:24])([F:23])[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:21][N:6]=[C:17]([NH2:18])[CH:16]=2)=[CH:11][CH:10]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 27237553-Methoxy-2-propenenitrileHCID 10942334Sodium MethoxideHCID 205348393-(4-(Trifluoromethyl)phenyl)-3,3-dimethoxypropionitrile

Product 1

HCID 130355455-[4-(Trifluoromethyl)phenyl]-1,2-oxazol-3-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

3-(4-Trifluoromethyl)phenyl)-3-methoxyacrylonitrile plus 3-(4-(trifluoromethyl)phenyl)-3,3-dimethoxypropionitrile (1330 grams as a mixture) and hydroxylamine.HCl (1180 grams) were dissolved in methanol and chilled to 20° C. in an ice-bath. Next sodium methylate (1890 grams) was added portion-wise over a one and one-half hour period keeping the temperature between 20°-30° C. The reaction mixture was then heated to reflux for about 17 hours and then cooled to 40° C. and filtered. After the filtrate was stripped and poured into ice-water with stirring, a light yellow solid precipitate formed which was filtered and identified by NMR analysis as the desired product, yield 994 grams.

Workup

  1. custombetween 20°-30° C
  2. temperatureThe reaction mixture was then heated
  3. temperatureto reflux for about 17 hours
  4. temperaturecooled to 40° C.
  5. filtrationfiltered
  6. additionpoured into ice-water
  7. customa light yellow solid precipitate formed which
  8. filtrationwas filtered

Sources & evidence

ORD record
ord-cd164b732ae54991aca8bb08aabab14a
Source dataset
uspto-grants-1982_06
Patent number
US04336264

Reaction notes

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