Hydrochloric Acid → 2-(4-(3,5-Dichlorophenylureido)phenoxy)-2-methylpropionic acid

HRID 1649934

Reaction equation

HRID 1649934 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][C:7]([CH3:12])([CH3:11])[C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.[Cl:15][C:16]1[CH:17]=[C:18]([N:23]=[C:24]=[O:25])[CH:19]=[C:20]([Cl:22])[CH:21]=1.O.Cl>N1C=CC=CC=1>[Cl:15][C:16]1[CH:17]=[C:18]([NH:23][C:24](=[O:25])[NH:1][C:2]2[CH:3]=[CH:4][C:5]([O:6][C:7]([CH3:12])([CH3:11])[C:8]([OH:10])=[O:9])=[CH:13][CH:14]=2)[CH:19]=[C:20]([Cl:22])[CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 944603,5-Dichlorophenyl isocyanateHCID 27749582-(4-Aminophenoxy)-2-methylpropanoic acid

Product 1

HCID 1953472-(4-(3,5-Dichlorophenylureido)phenoxy)-2-methylpropionic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirring solution of 4.95 g (0.025 mole) of 2-(4-aminophenoxy)-2-methylpropionic acid in 50 ml dry pyridine, 4.95 g (0.025 mole) of 3,5-dichlorophenyl isocyanate were added. After 1 hour stirring at room temperature, 150 ml water was added and the mixture was acidified with concentrated HCl. The precipitate was filtered, washed several times with cold water and dried. Recrystallization from aqueous acetone gave small plates 1.81 g (94%) MP 182-184°.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed several times with cold water
  3. customdried
  4. customRecrystallization from aqueous acetone
  5. customgave small plates 1.81 g (94%) MP 182-184°

Sources & evidence

ORD record
ord-388dc580be304e51a9ccab51f3795d39
Source dataset
uspto-grants-1990_05
Patent number
US04921997

Linked notes

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