Hydrochloric Acid → HCID 68607770, compound

HRID 1436651Notes

Reaction equation

HRID 1436651 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:13]=[C:12]([S:14](Cl)(=[O:16])=[O:15])[CH:11]=[C:6]([C:7]([O:9]C)=[O:8])[CH:5]=1.[CH3:19][NH:20][CH3:21].[OH-].[Na+].Cl>C1COCC1.C(OCC)(=O)C.CO>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:13]=[C:12]([S:14](=[O:16])(=[O:15])[N:20]([CH3:21])[CH3:19])[CH:11]=[C:6]([C:7]([OH:9])=[O:8])[CH:5]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 14798Sodium HydroxideHCID 37891971,3-Benzenedicarboxylic acid, 5-(chlorosulfonyl)-, 1,3-dimethyl ester

Product 1

HCID 68607770HCID 68607770, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve commercially available 5-chlorosulfonyl-isophthalic acid dimethyl ester (422 mg, 1.43 mmol) in THF (10 mL) and add dimethylamine (2.0 M in THF, 2.5 mL, 5 mmol). Stir at room temperature 3 h, dilute with ethyl acetate, wash with 10% aqueous potassium carbonate, 0.1 N citric acid and saturated aqueous sodium chloride. Dry (magnesium sulfate), filter and concentrate. Dissolve the residue in acetone (10 mL) and methanol (5 mL). Add a solution of NaOH (60 mg, 1.43 mmol) in methanol (0.7 mL). Stir at room temperature 16 h and acidify with 1 N HCl to about pH=1. Partition between ethyl acetate and water, dry (magnesium sulfate) and concentrate to give the title compound.

Workup

  1. washwash with 10% aqueous potassium carbonate, 0.1 N citric acid and saturated aqueous sodium chloride
  2. dry with materialDry (magnesium sulfate)
  3. filtrationfilter
  4. concentrationconcentrate
  5. dissolutionDissolve the residue in acetone (10 mL)
  6. stirringStir at room temperature 16 h
  7. customPartition between ethyl acetate and water
  8. dry with materialdry (magnesium sulfate)
  9. concentrationconcentrate

Sources & evidence

ORD record
ord-568d126a102248e8905d020f3cb7fdb9
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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