Methanesulfonic Acid → 2-Methylcyclohexyl 5-amino-2-chlorobenzoate

HRID 1292596Notes

Reaction equation

HRID 1292596 reaction equation
CS(O)(=O)=O.[NH2:6][C:7]1[CH:8]=[CH:9][C:10]([Cl:16])=[C:11]([CH:15]=1)[C:12]([OH:14])=[O:13].[CH3:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1O>>[NH2:6][C:7]1[CH:8]=[CH:9][C:10]([Cl:16])=[C:11]([CH:15]=1)[C:12]([O:14][CH:19]1[CH2:20][CH2:21][CH2:22][CH2:23][CH:18]1[CH3:17])=[O:13]

Participants

4

Reactant 3

HCID 6395Methanesulfonic AcidHCID 114182-MethylcyclohexanolHCID 378795-Amino-2-chlorobenzoic acid

Product 1

HCID 189158082-Methylcyclohexyl 5-amino-2-chlorobenzoateYield 81.4%

Procedure

Methanesulfonic acid (99%, 100 g, 1.0 mole) was added slowly to a stirred mixture of 5-amino-2-chlorobenzoic acid (85%, 100 g, 0.5 mole) in 2-methylcyclohexanol (200 g, 1.85 mole). The mixture was heated under reflux with stirring for 6 hours, then the excess 2-methylcyclohexanol was evaporated under reduced pressure. The residue was then dissolved in methylene chloride (800 ml), washed with water (300 ml), 5% sodium bicarbonate solution (300 ml), water (300 ml), dried (magnesium sulfate), and filtered. The solvent was then evaporated to give 109 g of 2-methylcyclohexyl 5-amino-2-chlorobenzoate as a light brown oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux
  3. customthe excess 2-methylcyclohexanol was evaporated under reduced pressure
  4. dissolutionThe residue was then dissolved in methylene chloride (800 ml)
  5. washwashed with water (300 ml), 5% sodium bicarbonate solution (300 ml), water (300 ml)
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. customThe solvent was then evaporated

Sources & evidence

ORD record
ord-162df2a6d7d34291938c0e2e70422065
Source dataset
uspto-grants-1998_05
Patent number
US05756813

Reaction notes

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