Thionyl Chloride → N-(2-hydroxy-4-methoxyphenyl)-2-bromo-5-methyl-3-thiophenecarboxamide

HRID 649983Notes

Reaction equation

HRID 649983 reaction equation
[Br:1][C:2]1[S:3][C:4]([CH3:10])=[CH:5][C:6]=1[C:7](Cl)=[O:8].BrC1SC(C)=CC=1C(O)=O.S(Cl)(Cl)=O.[NH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][C:27]=1[OH:34]>C1(C)C=CC=CC=1.N1C=CC=CC=1>[OH:34][C:27]1[CH:28]=[C:29]([O:32][CH3:33])[CH:30]=[CH:31][C:26]=1[NH:25][C:7]([C:6]1[CH:5]=[C:4]([CH3:10])[S:3][C:2]=1[Br:1])=[O:8]

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 99421632-Amino-5-methoxyphenolHCID 111175892-Bromo-5-methylthiophene-3-carboxylic acidHCID 184222542-Bromo-5-methyl-3-thiophenecarbonyl chloride

Product 1

HCID 10860794N-(2-hydroxy-4-methoxyphenyl)-2-bromo-5-methyl-3-thiophenecarboxamideYield 56.5%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 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-amino-5-methoxyphenol (2.0 g) in pyridine (50 ml) at 0° C. The mixture was stirred at room temperature for 2.5 hours and 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-4-methoxyphenyl)-2-bromo-5-methyl-3-thiophenecarboxamide (2.1 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-1c94d5856e89420f893e5855ffbaf56d
Source dataset
uspto-grants-2001_08
Patent number
US06271225B1

Reaction notes

Loading…