p-Toluidine → HCID 3651419, compound

HRID 605126Notes

Reaction equation

HRID 605126 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[CH:6][CH:7]=1.CCN(C(C)C)C(C)C.[F:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][C:20]=1[N+:28]([O-:30])=[O:29]>O1CCCC1.O>[F:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)=[O:24])=[CH:21][C:20]=1[N+:28]([O-:30])=[O:29]

Participants

6

Reactant 3

HCID 7813p-ToluidineHCID 81531DiisopropylethylamineHCID 27833474-Fluoro-3-nitrobenzoyl chloride

Product 1

HCID 3651419HCID 3651419, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of p-Tolylamine (626 mg, 5.89 mmol), and Hunig's base (2.054 ml, 11.8 mmol) in tetrahydrofuran (20 mL) was added the product from Example 86A (1.20 g, 5.89 mmol) in tetrahydrofuran (10 mL) dropwise over 10 minutes. The solution was stirred at room temperature for 1 hour, the reaction mixture diluted with water and the title compound was collected by filtration (1.77 g, 100%).

Workup

  1. filtrationthe title compound was collected by filtration (1.77 g, 100%)

Sources & evidence

ORD record
ord-7a77df977e0c4214ba992d09ad8adac5
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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