Hydrochloric Acid → HCID 10548134, compound

HRID 247908Notes

Reaction equation

HRID 247908 reaction equation
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]2[S:7][C:8]([C:14]([NH:16][C:17]3[CH:26]=[CH:25][C:20]([C:21]([O:23]C)=[O:22])=[CH:19][CH:18]=3)=[O:15])=[C:9]([O:10][CH:11]([CH3:13])[CH3:12])[C:5]=2[CH:4]=1.[OH-].[Na+].Cl>CO>[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]2[S:7][C:8]([C:14]([NH:16][C:17]3[CH:26]=[CH:25][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=3)=[O:15])=[C:9]([O:10][CH:11]([CH3:13])[CH3:12])[C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10668620HCID 10668620, compound

Product 1

HCID 10548134HCID 10548134, compoundYield 64.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4.0 g of methyl 4-[[[5-methoxy-3-(1-methylethoxy)-benzo[b]thien-2-yl]carbonyl]amino]benzoate and 2 g of 50% NaOH in 100 mL of 10% aqueous methanol is heated on a steam bath for 15 minutes, then poured onto ice and acidified with 10% HCl. The resulting gum is extracted into 500 mL of diethyl ether. The organic phase is dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude solid is triturated with t-butyl methyl ether to provide 2.5 g of product; mp 236°-239° C. (dec).

Workup

  1. temperatureis heated on a steam bath for 15 minutes
  2. additionpoured onto ice
  3. extractionThe resulting gum is extracted into 500 mL of diethyl ether
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude solid is triturated with t-butyl methyl ether

Sources & evidence

ORD record
ord-2950bcc2f92046cd92e1550c5d9446a4
Source dataset
uspto-grants-1993_05
Patent number
US05208253

Reaction notes

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