Ammonia → HCID 17985575, compound

HRID 1725395Notes

Reaction equation

HRID 1725395 reaction equation
[S:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][C:8]=2[CH2:10][C:11]([OH:13])=O)[CH:3]=[CH:2]1.[Cl-].[NH4+:15].N>C(O)C>[S:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][C:8]=2[CH2:10][C:11]([NH2:15])=[O:13])[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 67338156HCID 67338156, compound

Product 1

HCID 17985575HCID 17985575, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
-78 °C

Procedure

In a high pressure flask, dissolve (thieno[3,2-b]pyridin-7-yl)acetic acid (3.02 g, 13.65 mmol) in absolute ethanol (100 mL). Add ammonium chloride (1.09 g, 20.38 mmol) to the solution. Cool the solution to −78° C. Condense ammonia gas into the solution by bubbling (15 minutes at 10 psi). Seal the flask and slowly bring to ambient temperature. Stir the reaction at room temperature for 4 days. Cool the reaction vessel to −78° C. Open the flask and allow it to slowly return to ambient pressure. Filter the contents and wash with water (10 mL) to obtain the title compound as a white solid (1.46 g). Concentrate the filtrate and triturate the residue with diethyl ether. Filter and wash with water (5 mL) to obtain additional pure product (0.46 g).

Workup

  1. customby bubbling (15 minutes at 10 psi)
  2. customSeal the flask
  3. customslowly bring to ambient temperature
  4. customthe reaction at room temperature for 4 days
  5. temperatureCool the reaction vessel to −78° C
  6. filtrationFilter the contents
  7. washwash with water (10 mL)

Sources & evidence

ORD record
ord-9a287a32435742c88c2c5ff70602665f
Source dataset
uspto-grants-2009_02
Patent number
US07491716B2

Reaction notes

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