Water → HCID 10202916, compound

HRID 460534Notes

Reaction equation

HRID 460534 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.[CH:25]1[CH:30]=[CH:29][C:28]([N:31]=[C:32](Cl)Cl)=[CH:27][CH:26]=1.O>ClCCCl>[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[N:16]=[C:32]([NH:31][C:28]3[CH:29]=[CH:30][CH:25]=[CH:26][CH:27]=3)[N:17]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:12]=2[CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 12145Phenylimidocarbonyl chlorideHCID 120430856-(3-Phenylamino-4-aminophenyl)oxyhexanoic acid methyl ester

Product 1

HCID 10202916HCID 10202916, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

200 mg of 6-(3-phenylamino-4-aminophenyl)oxyhexanoic acid methyl ester was dissolved in 1 ml of 1,2-dichloroethane, the solution was mixed with 85 μl of phenylisocyanide dichloride, and the mixture was heated for 6 hours to 65° C. 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 purified by column chromatography on silica gel. 55 mg was obtained.

Workup

  1. temperaturethe mixture was heated for 6 hours to 65° C
  2. temperatureAfter cooling
  3. extractionextracted three times with ethyl acetate
  4. washthe combined organic phases were washed with saturated sodium chloride solution
  5. customdried on sodium sulfate
  6. concentrationconcentrated by evaporation in a vacuum
  7. customThe residue was purified by column chromatography on silica gel
  8. custom55 mg was obtained

Sources & evidence

ORD record
ord-71c1e81c6ad142e08a1e95de6dc0c3c6
Source dataset
uspto-grants-2007_03
Patent number
US07196202B2

Reaction notes

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