Urea → 6-[[1-Phenyl-2-oxo-2,3-dihydro-1H-benzoimidazol-6-yl]oxy]hexanoic acid methyl ester

HRID 460523

Reaction equation

HRID 460523 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[C:12]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:11]=1.N[C:26](N)=[O:27]>O>[CH3:1][O:2][C:3](=[O:24])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]2[NH:16][C:26](=[O:27])[N:17]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:12]=2[CH:11]=1

Participants

4

Reactant 2

HCID 1176UreaHCID 120430856-(3-Phenylamino-4-aminophenyl)oxyhexanoic acid methyl ester

Product 1

HCID 694331146-[[1-Phenyl-2-oxo-2,3-dihydro-1H-benzoimidazol-6-yl]oxy]hexanoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

7.5 g of 6-(3-phenylamino-4-aminophenyl)oxyhexanoic acid methyl ester was mixed with 8.23 g of urea, and the mixture was heated to 140° C. for 4 hours. After cooling, it was mixed with water, extracted three times with ethyl acetate, the combined organic phases were washed with saturated sodium chloride solution, dried on sodium sulfate and concentrated by evaporation in a vacuum. The residue was crystallized from diisopropyl ether. 4.27 g was obtained.

Workup

  1. temperatureAfter cooling
  2. extractionextracted three times with ethyl acetate
  3. washthe combined organic phases were washed with saturated sodium chloride solution
  4. customdried on sodium sulfate
  5. concentrationconcentrated by evaporation in a vacuum
  6. customThe residue was crystallized from diisopropyl ether
  7. custom4.27 g was obtained

Sources & evidence

ORD record
ord-5aa0404138ec4049b12c402df014f8e0
Source dataset
uspto-grants-2007_03
Patent number
US07196202B2

Linked notes

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