O-Toluidine → HCID 70922270, compound

HRID 524975Notes

Reaction equation

HRID 524975 reaction equation
ClC(Cl)(Cl)[C:3]([C:5]1[NH:6][CH:7]=[C:8]([CH3:10])[CH:9]=1)=[O:4].[NH2:13][C:14]1[C:15]([CH3:20])=[CH:16][CH:17]=[CH:18][CH:19]=1.C(N(CC)CC)C>CCCCCC>[CH3:10][C:8]1[CH:9]=[C:5]([C:3]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])=[O:4])[NH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7242O-ToluidineHCID 8471TriethylamineHCID 70922409HCID 70922409, compound

Product 1

HCID 70922270HCID 70922270, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 2,2,2-trichloro-1-(4-methyl-1H-pyrrol-2-yl)ethanone (2 g, 8.8 mmol) in a mixture of o-toluidine (1.76 mL, 16.5 mmol) and triethylamine (2.1 mL, 15.07 mmol) under argon was heated to 80° C. with stirring during 75 h. Afterwards, the reaction mixture was concentrated to dryness giving a residue that was treated with hexane and the resulting solid filtered to afford 848 mg of the title compound (45% yield).

Workup

  1. concentrationAfterwards, the reaction mixture was concentrated to dryness
  2. customgiving a residue that
  3. filtrationthe resulting solid filtered

Sources & evidence

ORD record
ord-c7e70a85971b4183999c5a069e4e05d2
Source dataset
uspto-grants-2016_05
Patent number
US09340547B2

Reaction notes

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