3-(Trifluoromethyl)phenyl isocyanate → 1-(4-Iodo-3-methylphenyl)-3-(3-(trifluoromethyl)phenyl)urea

HRID 1042653Notes

Reaction equation

HRID 1042653 reaction equation
[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[CH3:9].[N:10]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=1)=[C:11]=[O:12].[N-]=C=O>C1C=CC=CC=1>[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:11]([NH:10][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:20])([F:21])[F:22])[CH:14]=2)=[O:12])=[CH:4][C:3]=1[CH3:9]

Participants

5

Reactant 3

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 105034IsocyanateHCID 27342754-Iodo-3-methylaniline

Product 1

HCID 684617451-(4-Iodo-3-methylphenyl)-3-(3-(trifluoromethyl)phenyl)urea

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4-iodo-3-methylaniline (200 mg, 0.86 mmol) in benzene (5 mL) in a sealable tube was added 1-isocyanato-3-(trifluoromethyl)benzene (0.133 mL, 0.94 mL; “E” is an electrophilic group discussed in scheme 3, and here is an isocyanate). The tube was sealed and heated at 90° C. for 4 h. The mixture was allowed to cool to room temperature before filtering. The off white solid was washed with additional benzene (10 mL) and used without further purification.

Workup

  1. customThe tube was sealed
  2. temperatureto cool to room temperature
  3. filtrationbefore filtering
  4. washThe off white solid was washed with additional benzene (10 mL)
  5. customused without further purification

Sources & evidence

ORD record
ord-098ec6bc6b8846d3a551d7c66a126e4c
Source dataset
uspto-grants-2013_10
Patent number
US08557996B2

Reaction notes

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