Pyridine → N-(2-hydroxy-6-methylphenyl)-2-bromo-5-methyl-3-thiophenecarboxamide

HRID 649984Notes

Reaction equation

HRID 649984 reaction equation
[Br:1][C:2]1[S:3][C:4]([CH3:10])=[CH:5][C:6]=1[C:7](Cl)=[O:8].BrC1S[C:14]([CH3:20])=[CH:15][C:16]=1[C:17]([OH:19])=O.S(Cl)(Cl)=O.C(OC(C)C)(C)C.[C:32](OCC)(=O)C.[N:38]1C=CC=C[CH:39]=1>C1(C)C=CC=CC=1>[OH:19][C:17]1[CH:16]=[CH:15][CH:14]=[C:20]([CH3:32])[C:39]=1[NH:38][C:7]([C:6]1[CH:5]=[C:4]([CH3:10])[S:3][C:2]=1[Br:1])=[O:8]

Participants

7

Reactant 5

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 111175892-Bromo-5-methylthiophene-3-carboxylic acidHCID 184222542-Bromo-5-methyl-3-thiophenecarbonyl chlorideHCID 22281796Diisopropylether ethyl acetate

Product 1

HCID 11110188N-(2-hydroxy-6-methylphenyl)-2-bromo-5-methyl-3-thiophenecarboxamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

2-Bromo-5-methyl-3-thiophenecarbonyl chloride (2.6 g), prepared in the same manner as above from 2-bromo-5-methyl-3-thiophenecarboxylic acid and thionyl chloride, was suspended in toluene (20 ml). This toluene solution was added dropwise to a solution of 2-ainino-3-methylphenol (1.4 g) in pyridine (30 ml) at 0° C. The mixture was stirred at room temperature for 3 hours and diisopropyl ether-ethyl acetate was added. The solvent was evaporated under reduced pressure. The precipitated crystals were collected by filtration, and washed with diluted hydrochloric acid and diisopropyl ether to give N-(2-hydroxy-6-methylphenyl)-2-bromo-5-methyl-3-thiophenecarboxamide (3.0 g).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. filtrationThe precipitated crystals were collected by filtration
  3. washwashed with diluted hydrochloric acid and diisopropyl ether

Sources & evidence

ORD record
ord-f67697fa8a1b4177a052361414b52f81
Source dataset
uspto-grants-2001_08
Patent number
US06271225B1

Reaction notes

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