Hydrochloric Acid → Methyl 4-[[[5-Methoxy-3-(1-methylethoxy)benzo[b]thien-2-yl]carbonyl]amino]benzeneacetate

HRID 247909Notes

Reaction equation

HRID 247909 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]2[S:7][C:8]([C:14]([OH:16])=O)=[C:9]([O:10][CH:11]([CH3:13])[CH3:12])[C:5]=2[CH:4]=1.C(Cl)(=O)C(Cl)=O.Cl.[NH2:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][C:34]([O:36][CH3:37])=[O:35])=[CH:29][CH:28]=1.C(N(CC)CC)C>O1CCCC1.CN(C)C=O>[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]2[S:7][C:8]([C:14]([NH:26][C:27]3[CH:28]=[CH:29][C:30]([CH2:33][C:34]([O:36][CH3:37])=[O:35])=[CH:31][CH:32]=3)=[O:16])=[C:9]([O:10][CH:11]([CH3:12])[CH3:13])[C:5]=2[CH:4]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 2761030Methyl 2-(4-aminophenyl)acetateHCID 139616485-Methoxy-3-(1-methylethoxy)benzo[b]thiophene-2-carboxylic acid

Product 1

HCID 19390216Methyl 4-[[[5-Methoxy-3-(1-methylethoxy)benzo[b]thien-2-yl]carbonyl]amino]benzeneacetateYield 84%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To 5-methoxy-3-(1-methylethoxy)benzo[b]thiophene-2-carboxylic acid (500 mg, 2.0 mmoles) in 20 mL of dry tetrahydrofuran is added oxalyl chloride (262 μL, 3.0 mmoles) followed by one drop of dimethylformamide. The HCl salt of methyl 4-aminophenylacetate (605 mg, 3.0 mmoles) is added, followed by triethylamine (1.4 mL, 10 mmoles). The mixture is stirred at room temperature overnight. The mixture is partitioned between ethyl acetate and 1N HCl. The organic layer is washed with water, then brine. The organic layer is next dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude product is purified by flash chromatography, eluting with a gradient of 1:1 ethyl acetate:hexane to only ethyl acetate to provide 692 mg (84%) of product; mp 111°-113° C.

Workup

  1. customThe mixture is partitioned between ethyl acetate and 1N HCl
  2. washThe organic layer is washed with water
  3. dry with materialThe organic layer is next dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product is purified by flash chromatography
  7. washeluting with a gradient of 1:1 ethyl acetate

Sources & evidence

ORD record
ord-000bab3bdbe5406283f57d6226024e7a
Source dataset
uspto-grants-1993_05
Patent number
US05208253

Reaction notes

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