Toluene → HCID 18931238, compound

HRID 1598994Notes

Reaction equation

HRID 1598994 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([C:8]1[CH:13]=[C:12]([NH2:14])[C:11]([O:15][CH3:16])=[CH:10][C:9]=1[O:17][CH3:18])=[O:7].[F:19][C:20]([F:31])([F:30])[C:21]1[CH:26]=[CH:25][C:24]([N:27]=[C:28]=[O:29])=[CH:23][CH:22]=1.C1(C)C=CC=CC=1>C(OCC)(=O)C>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([C:8]1[C:9]([O:17][CH3:18])=[CH:10][C:11]([O:15][CH3:16])=[C:12]([NH:14][C:28]([NH:27][C:24]2[CH:23]=[CH:22][C:21]([C:20]([F:19])([F:30])[F:31])=[CH:26][CH:25]=2)=[O:29])[CH:13]=1)=[O:7]

Participants

5

Reactant 3

HCID 1140TolueneHCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 18931134HCID 18931134, compound

Product 1

HCID 18931238HCID 18931238, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 5-chloro-1-(5-amino-2,4-dimethoxyphenyl)-1-pentanone (0.27 g, 1 mmol), prepared as in Example 14, α,α,α-trifluoro-p-tolyl isocyanate (0.16 mL, 1.1 mmol), toluene (3 mL) and ethyl acetate (0.5 mL) was heated 10 minutes with stirring at approximately 50° C. The mixture was concentrated and the residue was recrystallized from hexane/ethyl acetate. The solids were collected and dried at 70° C. to give 1-[5-(5-chloropentanoyl)-2,4-dimethoxyphenyl]-3-(4-trifluoromethylphenyl)urea (0.43 g, 0.94 mmol), m.p. 154°-156° C.

Workup

  1. temperaturewas heated 10 minutes
  2. concentrationThe mixture was concentrated
  3. customthe residue was recrystallized from hexane/ethyl acetate
  4. customThe solids were collected
  5. customdried at 70° C.

Sources & evidence

ORD record
ord-e68df60f4fb34624b0a7d08cabac56ad
Source dataset
uspto-grants-1998_04
Patent number
US05739336

Reaction notes

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