Hydrochloric Acid → HCID 178517033, compound

HRID 2352893Notes

Reaction equation

HRID 2352893 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][C:6]([CH2:11][C:12]3[CH:13]=[C:14]([NH:18][C:19]([C:21]4[S:22][CH:23]=[CH:24][CH:25]=4)=[O:20])[CH:15]=[CH:16][CH:17]=3)=[CH:7][CH:8]=2)[NH:3]1.[CH:26](OCC)=[O:27].[O-]CC.[Na+].Cl>C(O)C>[OH:27][CH:26]=[C:10]1[C:9]2[C:4](=[CH:5][C:6]([CH2:11][C:12]3[CH:13]=[C:14]([NH:18][C:19]([C:21]4[S:22][CH:23]=[CH:24][CH:25]=4)=[O:20])[CH:15]=[CH:16][CH:17]=3)=[CH:7][CH:8]=2)[NH:3][C:2]1=[O:1]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8025Ethyl formateHCID 2723922Sodium ethoxideHCID 86610409HCID 86610409, compound

Product 1

HCID 178517033HCID 178517033, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
78 °C

Procedure

Thiophene-2-carboxylic acid [3-(2-oxo-2,3-dihydro-1H-indol-6-ylmethyl)-phenyl]-amide (0.110 g, 0.306 mmol) and ethyl formate (0.075 mL, 0.918 mmol) were dissolved in anhydrous ethanol (0.6 mL). The resulting solution was treated in dropwise fashion with a 21 wt % solution of sodium ethoxide in ethanol (2.85 mL, 1.53 mmol). This reaction mixture was heated at 78° C. for 1 h, producing a black oil. Subsequently, the reaction mixture was cooled to room temperature, and then the reaction pH was adjusted to pH 1 with dropwise addition of 1M HCl(aq) causing the formation of a pale brown precipitate. The suspension was filtered yielding a tan solid as the pure Thiophene-2-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indol-6-ylmethyl)-phenyl]-amide (0.061 g, 0.162 mmol, 53%).

Workup

  1. customproducing a black oil
  2. temperatureSubsequently, the reaction mixture was cooled to room temperature
  3. filtrationThe suspension was filtered

Sources & evidence

ORD record
ord-b2ce6efd8d554f3aacb1ffbeaf72a03e
Source dataset
uspto-grants-2010_07
Patent number
US07749530B2

Reaction notes

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