Ethyl Acetate → HCID 59770082, compound

HRID 2390251Notes

Reaction equation

HRID 2390251 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[NH2:5].[CH3:10][S:11](Cl)(=[O:13])=[O:12].CCOC(C)=O>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][S:11]([CH3:10])(=[O:13])=[O:12])[CH:6]=[CH:7][C:8]=1[CH3:9]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 82187Benzenamine, 3-bromo-4-methyl-

Product 1

HCID 59770082HCID 59770082, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A cooled (0° C.) solution of 3-bromo-4-methylaniline (ABCR; 1.00 g; 5.37 mmol) in pyridine (20 ml) was treated with methanesulfonyl chloride (500 μl; 6.45 mmol). The reaction mixture was allowed to warm to RT and stirred for 1 hour, then EtOAc was added and the organic layer was washed with a 1N aqueous solution of HCl. The organic layer was dried over MgSO4, filtered and concentrated to dryness to give the title compound as a brown solid (1.42 g, quantitative).

Workup

  1. washthe organic layer was washed with a 1N aqueous solution of HCl
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-17f639d0649d45f58d0eae0bde4d97b5
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

Loading…