3-(Trifluoromethyl)aniline → N-(2-chloroethyl)-N'-[3-(trifluoromethyl)phenyl]urea

HRID 572436Notes

Reaction equation

HRID 572436 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([NH2:9])[CH:6]=[CH:7][CH:8]=1.[Cl:12][CH2:13][CH2:14][N:15]=[C:16]=[O:17]>C1(C)C=CC=CC=1>[Cl:12][CH2:13][CH2:14][NH:15][C:16]([NH:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=1)=[O:17]

Participants

4

Reactant 2

HCID 73753-(Trifluoromethyl)anilineHCID 160352-Chloroethyl isocyanate

Product 1

HCID 276667N-(2-chloroethyl)-N'-[3-(trifluoromethyl)phenyl]ureaYield 96%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Using analogous reagents and reaction conditions as described in Example 1 above, 3-trifluoromethyl-phenylamine (2.0 g, 12.412 mmol) in toluene (20 mL) was reacted with 1-chloro-2-isocyanatoethane (1.96 g, 18.618 mmol to give 3.2 g of pure product (96%)

Workup

  1. customreagents and reaction conditions

Sources & evidence

ORD record
ord-57c089001175415c92bcf0bd1c1b4a05
Source dataset
uspto-grants-2015_05
Patent number
US09029399B2

Reaction notes

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