2-(Trifluoromethyl)aniline → HCID 13070054, compound

HRID 1759596Notes

Reaction equation

HRID 1759596 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([F:11])([F:10])[F:9].[S-:12][C:13]#[N:14].[Na+].BrBr.[Br-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CO.C(Cl)Cl.O>[S:12]([C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[C:3]([C:8]([F:9])([F:10])[F:11])[CH:4]=1)[C:13]#[N:14]

Participants

9

Reactant 5

HCID 69222-(Trifluoromethyl)anilineHCID 10340Sodium CarbonateHCID 24408Bromine2×HCID 253881Sodium BromideHCID 516871Sodium thiocyanate

Product 1

HCID 13070054HCID 13070054, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a cold (0°-5° C.) stirred solution of 2-aminobenzotrifluoride (6.44 g., 0.04 mole) and sodium thiocyanate (9.72 g., 0.12 mole) in methanol (100 ml) is added dropwise a solution of bromine (6.6 g., 0.42 mole) in methanol (25 ml) saturated with sodium bromide. The solution is stirred for 20 minutes following the addition of bromine and then poured into water (750 ml) and neutralized with sodium carbonate. The resulting oil is taken up in methylene chloride and dried. Removal of the drying agent and solvent gives 4-thiocyano-2-trifluoromethylaniline as an oil that solidifies on standing (8.4 g., 96 percent yield). A purified sample has a melting point of 52°-55° C. and the following analysis:

Workup

  1. customdried
  2. customRemoval of the drying agent and solvent

Sources & evidence

ORD record
ord-4a9936609dae4290b7e7a8391a1f5cc3
Source dataset
uspto-grants-1982_07
Patent number
US04341901

Reaction notes

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