Hydrochloric Acid → HCID 12848748, compound

HRID 1065149Notes

Reaction equation

HRID 1065149 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].N1C=CC=CC=1.[CH3:20][S:21](Cl)(=[O:23])=[O:22].Cl>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([NH:13][S:21]([CH3:20])(=[O:23])=[O:22])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 89843Methyl 5-amino-o-anisate

Product 1

HCID 12848748HCID 12848748, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 2-methoxy-5-aminobenzoate (300 mg) and dry pyridine (3 ml), methanesulfonyl chloride (210 mg) is added dropwise with ice cooling and stirring, and the resultant mixture is stirred at room temperature for 1 hour. The reaction mixture is acidified with 6 N hydrochloric acid and shaken with methylene chloride. The organic layer is washed with water, dried over sodium sulfate, and evaporated under reduced pressure to remove the methylene chloride. The residue is chromatographed on a column of silica gel, which is eluted with methylene chloride - 2% methanol/methylene chloride, and the eluate is evaporated to remove the solvent. The residue is recrystallized from ethyl acetate/isopropyl ether to give methyl 2-methoxy-5-methanesulfonamidobenzoate (381 mg) as colorless prisms melting at 84° to 86° C.

Workup

  1. washThe organic layer is washed with water
  2. dry with materialdried over sodium sulfate
  3. customevaporated under reduced pressure
  4. customto remove the methylene chloride
  5. customThe residue is chromatographed on a column of silica gel, which
  6. washis eluted with methylene chloride - 2% methanol/methylene chloride
  7. customthe eluate is evaporated
  8. customto remove the solvent
  9. customThe residue is recrystallized from ethyl acetate/isopropyl ether

Sources & evidence

ORD record
ord-94b83a8bd5db422c82f83603fd0011ba
Source dataset
uspto-grants-1982_05
Patent number
US04328344

Reaction notes

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