Water → HCID 21876330, compound

HRID 967846Notes

Reaction equation

HRID 967846 reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][OH:13])=[CH:7][CH:6]=1.[C:18](Cl)(=[O:21])[CH2:19][CH3:20].O.[C:24]1(C)[CH:29]=CC=C[CH:25]=1>>[C:18]([O:13][CH2:12][CH2:11][C:8]1[CH:7]=[CH:6][C:5]([N:4]2[C:3]3[CH:14]=[CH:15][CH:16]=[CH:17][C:2]=3[N:1]=[C:25]2[CH2:24][CH3:29])=[CH:10][CH:9]=1)(=[O:21])[CH2:19][CH3:20]

Participants

5

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 62324Propionyl chlorideHCID 21876484HCID 21876484, compound

Product 1

HCID 21876330HCID 21876330, compoundYield 58%

Procedure

To a stirred suspension of 2-[4-(2-aminoanilino)phenyl]ethanol (1.6 g, 7 mmol) in toluene (70 mL) was added propionyl chloride (1.5 g, 16 mmol) dropwise at 0° C., and the reaction mixture was heated at reflux temperature for 2 h. After cooling, the mixture was poured into water (50 mL) and extracted with ethyl acetate (100 mL). The organic layer was washed with 2N aqueous NaOH (50 mL) and brine (50 mL), then dried (MgSO4). Removal of solvent gave 1.3 g (58%) of the title compound as brown solids: MS (EI) m/z 322 (M+)

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux temperature for 2 h
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate (100 mL)
  5. washThe organic layer was washed with 2N aqueous NaOH (50 mL) and brine (50 mL)
  6. dry with materialdried (MgSO4)
  7. customRemoval of solvent

Sources & evidence

ORD record
ord-b68ea7d9d97c448c9759e7f83bff4a30
Source dataset
uspto-grants-2005_10
Patent number
US06956050B2

Reaction notes

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