P-Anisidine → HCID 56652487, compound

HRID 1184940Notes

Reaction equation

HRID 1184940 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[CH3:15][O:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:21][C:20]2[CH:22]=[CH:23][C:17]([O:16][CH3:15])=[CH:18][CH:19]=2)=[O:10])=[CH:4][C:3]=1[C:11]([F:12])([F:13])[F:14]

Participants

4

Reactant 2

HCID 7732P-AnisidineHCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzene

Product 1

HCID 56652487HCID 56652487, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-chloro-4-isocyanato-2-(trifluoromethyl)benzene (5.15 g, 26 mmol, 1.05 eq) was dissolved in dichloromethane (30 mL). A solution of p-methoxyaniline (3.07 g, 25 mmol, 1 eq) in dichloromethane (20 mL) was added dropwise and the mixture was stirred at room temperature for 20 hours. The mixture was filtered and washed with dichloromethane (5 mL×2). The solid was dissolved in ethyl acetate (50 mL), and the resulted solution was washed with diluted hydrochloric acid (1 N, 10 mL) and saturated brine (20 mL). The organic phase was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure to give 1-(4-chloro-3-trifluoromethylphenyl)-3-(4-methoxyphenyl)urea A6 (4.5 g, yield 52%) as a white solid.

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with dichloromethane (5 mL×2)
  3. dissolutionThe solid was dissolved in ethyl acetate (50 mL)
  4. washthe resulted solution was washed with diluted hydrochloric acid (1 N, 10 mL) and saturated brine (20 mL)
  5. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-41906517d4ac448dbbe6993c2e19c8e8
Source dataset
uspto-grants-2014_03
Patent number
US08669369B2

Reaction notes

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