Hydrochloric Acid → HCID 178484916, compound

HRID 651530Notes

Reaction equation

HRID 651530 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH2:9][O:10][C:11]2[CH:12]=[C:13]([O:18][S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:28])(=[O:21])=[O:20])[CH:14]=[C:15]([CH3:17])[CH:16]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2].[ClH:29].Cl.[CH3:31][NH2:32].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl.C(O)C>[ClH:28].[CH3:31][NH:32][C:1]([C:3]1[CH:4]=[C:5]([CH2:9][O:10][C:11]2[CH:12]=[C:13]([O:18][S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:29])(=[O:21])=[O:20])[CH:14]=[C:15]([CH3:17])[CH:16]=2)[CH:6]=[CH:7][CH:8]=1)=[NH:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 6364545Methylamine hydrochlorideHCID 540597372-Chlorobenzenesulfonic acid 3-[(3-cyanophenyl)methoxy]-5-methylphenyl ester

Product 1

HCID 178484916HCID 178484916, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-chlorobenzenesulfonic acid 3-[(3-cyanophenyl)methoxy]-5-methylphenyl ester (414 mg, 1.0 mmol), as prepared in step (a) of Example 6, in methylene chloride (10 mL) was added 37% HCl in ethanol (15 mL) at 0° C. The mixture was allowed to stand at 0° C. for 3 days. The solvent was evaporated and the residue was concentrated in vacuo from methylene chloride several times. The residue was dissolved in ethanol (10 mL), treated with methylamine hydrochloride (270 mg, 4.0 mmol) and Na2CO3 (212 mg, 2.0 mmol), and then stirred at room temperature for 2 days. The reaction mixture was partitioned between methylene chloride (150 mL) and 10% K2CO3. The organic phase was washed with 10% K2CO3 (50 mL) and dried over K2CO3. After removing the solvent in vacuo, HCl in methanol (30 mL) was added and the solvent was removed in vacuo. The residue was then purified by flash column chromatography (10% methanol/methylene chloride) and crystallized from methanol/ethyl acetate to give the title compound as white crystals (145 mg, 30%).

Workup

  1. customThe solvent was evaporated
  2. concentrationthe residue was concentrated in vacuo from methylene chloride several times
  3. dissolutionThe residue was dissolved in ethanol (10 mL)
  4. customThe reaction mixture was partitioned between methylene chloride (150 mL) and 10% K2CO3
  5. washThe organic phase was washed with 10% K2CO3 (50 mL)
  6. dry with materialdried over K2CO3
  7. customAfter removing the solvent in vacuo, HCl in methanol (30 mL)
  8. additionwas added
  9. customthe solvent was removed in vacuo
  10. customThe residue was then purified by flash column chromatography (10% methanol/methylene chloride)
  11. customcrystallized from methanol/ethyl acetate

Sources & evidence

ORD record
ord-a1fc95564c364d199bb080403b6ce557
Source dataset
uspto-grants-2001_08
Patent number
US06281206B1

Reaction notes

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