Hydrochloric Acid → 4-(4,4-Dimethyl-4,5-dihydro-1,3-oxazol-2-yl)aniline

HRID 1980188Notes

Reaction equation

HRID 1980188 reaction equation
[CH3:1][C:2]([NH:6][C:7](=[O:15])[C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=1)([CH3:5])[CH2:3]O.Cl>COCCOC>[NH2:14][C:11]1[CH:10]=[CH:9][C:8]([C:7]2[O:15][CH2:3][C:2]([CH3:1])([CH3:5])[N:6]=2)=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 20437346HCID 20437346, compound

Product 1

HCID 33197764-(4,4-Dimethyl-4,5-dihydro-1,3-oxazol-2-yl)aniline

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 9.5 g. of N-(1,1-dimethyl-2-hydroxyethyl)-4-aminobenzamide in 100 ml. of DME was added gaseous HCl such that all of the starting amide came out of solution. The solvent was removed and 30 ml. of thionyl chloride added. This solution was stirred for 2 days at 5° C. The excess thionyl chloride was removed. The amber liquid was then poured into 200 ml. of CH2Cl2 and neutralized with 20% NaOH with cooling. The solution was extracted with diethyl ether and the ether layer dried over MgSO4. The combined ether layer was filtered and concentrated to a solid; 5.75 g. This solid was preabsorbed on 25 g. of silica III and placed on 425 g. of silica (in a column). Elution with ether gave 3.7 g. of product which was recrystallized from CH2Cl2 -hexane (1:1) and acetonitrile, m.p. 227°-230° C.

Workup

  1. customThe solvent was removed
  2. additionof thionyl chloride added
  3. customThe excess thionyl chloride was removed
  4. additionThe amber liquid was then poured into 200 ml
  5. temperatureof CH2Cl2 and neutralized with 20% NaOH with cooling
  6. extractionThe solution was extracted with diethyl ether
  7. dry with materialthe ether layer dried over MgSO4
  8. filtrationThe combined ether layer was filtered
  9. concentrationconcentrated to a solid
  10. customThis solid was preabsorbed on 25 g
  11. washElution with ether
  12. customgave 3.7 g
  13. customof product which was recrystallized from CH2Cl2 -hexane (1:1) and acetonitrile, m.p. 227°-230° C.

Sources & evidence

ORD record
ord-5c33883632164e9489ece802588f7626
Source dataset
uspto-grants-1984_11
Patent number
US04485105

Reaction notes

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