1,2-Dichloroethane → HCID 10181944, compound

HRID 460535Notes

Reaction equation

HRID 460535 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](C2C=CC(C)=CC=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.Cl[CH2:37][CH2:38]Cl>>[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:16]([C:13]3[CH:14]=[CH:15][C:37]([CH3:38])=[CH:11][CH:12]=3)[C:12]=2[CH:11]=1

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 962WaterHCID 12145Phenylimidocarbonyl chlorideHCID 69434854HCID 69434854, compound

Product 1

HCID 10181944HCID 10181944, compound

Procedure

250 mg of 6-[3-(4-methylphenyl)-4-aminophenyl]oxyhexanoic acid methyl ester was dissolved in 1 ml of 1,2-dichloroethane, the solution was mixed with 0.1 ml of phenylisocyanide dichloride, and the mixture was heated for 8 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 crystallized from a mixture that consists of ethyl acetate and diethyl ether. 147 mg was obtained.

Workup

  1. temperaturethe mixture was heated for 8 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 crystallized from a mixture that
  8. custom147 mg was obtained

Sources & evidence

ORD record
ord-fe3a34419aef4d46aa123b2c7cd9d264
Source dataset
uspto-grants-2007_03
Patent number
US07196202B2

Reaction notes

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