Methanol → Chloramben-methyl

HRID 1992189Notes

Reaction equation

HRID 1992189 reaction equation
[NH2:1][C:2]1[C:3]([Cl:12])=[C:4]([CH:8]=[C:9]([Cl:11])[CH:10]=1)[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[OH-].[Na+].[CH3:20]O>O>[NH2:1][C:2]1[C:3]([Cl:12])=[C:4]([CH:8]=[C:9]([Cl:11])[CH:10]=1)[C:5]([O:7][CH3:20])=[O:6]

Participants

6

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 8630ChlorambenHCID 14798Sodium Hydroxide

Product 1

HCID 23714Chloramben-methylYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-amino-2,5-dichlorobenzoic acid (5.00 g, 24.27 mmol) was stirred in methanol (30 ml) at room temperature. Sulfuric Acid (5 ml) was added dropwise. Reaction stirred for 3 hours and was then diluted with water (30 ml) and basified using sodium hydroxide. Mixture was extracted with ethyl acetate×3. Solvent was removed to afford methyl 3-amino-2,5-dichlorobenzoate (4.20 g, 79%) as a solid.

Workup

  1. customReaction
  2. extractionMixture was extracted with ethyl acetate×3
  3. customSolvent was removed

Sources & evidence

ORD record
ord-c0e570a387ad4101a2a1356e4894235d
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

Loading…