Hydrochloric Acid → HCID 22620964, compound

HRID 430431Notes

Reaction equation

HRID 430431 reaction equation
[CH2:1]([N:3]([C:8]1[CH:18]=[C:17]([S:19]([CH3:22])(=[O:21])=[O:20])[CH:16]=[CH:15][C:9]=1[C:10]([O:12]CC)=[O:11])[S:4]([CH3:7])(=[O:6])=[O:5])[CH3:2].O.[OH-].[Li+].Cl>C(O)C>[CH2:1]([N:3]([C:8]1[CH:18]=[C:17]([S:19]([CH3:22])(=[O:20])=[O:21])[CH:16]=[CH:15][C:9]=1[C:10]([OH:12])=[O:11])[S:4]([CH3:7])(=[O:6])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 22620968HCID 22620968, compound

Product 1

HCID 22620964HCID 22620964, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 2-(N-ethyl-N-methylsulphonylamino)-4-methylsulphonylbenzoate (11.4 g) and lithium hydroxide monohydrate (1.37 g) in aqueous ethanol (50%) was stirred at room temperature for 19 hours. The mixture was then acidified with conc. hydrochloric acid and extracted with ethyl acetate. The combined organic extracts were dried (magnesium sulphate), filtered and evaporated to yield 2-(N-ethyl-N-methylsulphonylamino)-4-methylsulphonylbenzoic acid as a brown solid (9.48 g), NMR (acetone-d6); 1.15(t,3H), 2.98(s,3H), 3.22(s.3H), 3.85(q,2H), 8.0-8.25(m,3H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic extracts were dried (magnesium sulphate)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-cd1200984aaf4c78a3063174edcc4d38
Source dataset
uspto-grants-2001_11
Patent number
US06323155B1

Reaction notes

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