Hydrochloric Acid → HCID 89767826, compound

HRID 591490Notes

Reaction equation

HRID 591490 reaction equation
Cl.[Cl:2][C:3]1[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:4]=1[CH2:5][O:6][C:7]1[CH:26]=[CH:25][C:10]2[C:11]([O:21]COC)=[C:12]([C:14]([NH:16][CH2:17][CH2:18][O:19][CH3:20])=[O:15])[S:13][C:9]=2[CH:8]=1.C([O-])(O)=O.[Na+]>C1COCC1>[Cl:2][C:3]1[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:4]=1[CH2:5][O:6][C:7]1[CH:26]=[CH:25][C:10]2[C:11]([OH:21])=[C:12]([C:14]([NH:16][CH2:17][CH2:18][O:19][CH3:20])=[O:15])[S:13][C:9]=2[CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 118656102HCID 118656102, compound

Product 1

HCID 89767826HCID 89767826, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6M HCl (3 mL), 6-((2,4-dichlorobenzyl)oxy)-N-(2-methoxyethyl)-3-(methoxymethoxy)-1-benzothiophene-2-carboxamide (170 mg) and THF (10 mL) was stirred at room temperature for 4 h. To the mixture was added saturated aqueous NaHCO3, and the mixture was extracted with EtOAc. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was collected by filtration and washed with hexane to give the title compound (150 mg). The obtained crystals were recrystallized from acetone-hexane.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. filtrationThe residue was collected by filtration
  7. washwashed with hexane

Sources & evidence

ORD record
ord-9bc95d3c8bd943f5a445bfa6a5cef2d0
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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