Hydrochloric Acid → HCID 13020006, compound

HRID 1277818Notes

Reaction equation

HRID 1277818 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]([N:17]([CH2:19][CH:20](OC)OC)[CH3:18])=[O:16])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>O>[CH3:18][N:17]1[CH:19]=[CH:20][N:14]([C:11]2[CH:10]=[CH:9][C:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:13][CH:12]=2)[C:15]1=[O:16]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 13020004HCID 13020004, compound

Product 1

HCID 13020006HCID 13020006, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-(4-Phenoxyphenyl)-N'-(2,2-dimethoxyethyl)-N'-methylurea (5.0 grams, 0.015 mole), water (30 ml) and concentrated hydrochloric acid (3 ml) were charged into a glass reaction vessel fitted with a mechanical stirrer thermometer and condenser. The reaction mixture was refluxed for a period of about 15 minutes, cooled and extracted with ethyl acetate. The ethyl acetate solution was washed with dilute aqueous sodium bicarbonate and with portions of water and dried. The ethyl acetate was removed by mild warming under reduced pressure to yield a residue. This was recrystallized from ethyl acetate to yield the desired product 1-methyl-3-(4-phenoxyphenyl)-4-imidazolin-2-one as a solid having a melting point of 112° C.

Workup

  1. customfitted with a mechanical stirrer thermometer and condenser
  2. temperatureThe reaction mixture was refluxed for a period of about 15 minutes
  3. temperaturecooled
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate solution was washed with dilute aqueous sodium bicarbonate and with portions of water
  6. customdried
  7. customThe ethyl acetate was removed
  8. temperatureby mild warming under reduced pressure
  9. customto yield a residue
  10. customThis was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-330ba492c03448bc856b722bf356a075
Source dataset
uspto-grants-1981_07
Patent number
US04279637

Reaction notes

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