Sodium Hydroxide → HCID 136151230, compound

HRID 1363066Notes

Reaction equation

HRID 1363066 reaction equation
[CH2:1]([O:3][CH:4]([N:6]1[C:10]2[S:11][C:12]([C:14]([O:16]CC)=[O:15])=[CH:13][C:9]=2[C:8]([C:19]2[NH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N:7]1)[CH3:5])[CH3:2].[OH-].[Na+]>C(O)C>[CH2:1]([O:3][CH:4]([N:6]1[C:10]2[S:11][C:12]([C:14]([OH:16])=[O:15])=[CH:13][C:9]=2[C:8]([C:19]2[NH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N:7]1)[CH3:5])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 136151231HCID 136151231, compound

Product 1

HCID 136151230HCID 136151230, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.53 g (1.38 mmol) of ethyl 1-(1-ethoxyethyl)-3-(1H-indol-2-yl)-1H-thieno[2,3-c]pyrazole-5-carboxylate is dissolved with stirring in 40 cm3 of ethanol at a temperature in the region of 20° C. 2.8 cm3 (2.8 mmol) of 1N sodium hydroxide solution are then run in, and the resulting solution is then refluxed for 2 hours. The reaction medium is then concentrated to dryness under reduced pressure (2.7 kPa) and the residue is taken up in 30 cm3 of water to which is added 0.17 g of citric acid. The mixture is extracted with twice 50 cm3 of dichloromethane, and acidification of the aqueous phase is continued by addition of citric acid down to pH 2, and the extraction is then continued with twice 50 cm3 of dichloromethane. The various organic phases are combined, dried and then evaporated to dryness under reduced pressure (2.7 kPa). 0.46 g of 1-(1-ethoxyethyl)-3-(1H-indol-2-yl)-1H-thieno[2,3-c]pyrazole-5-carboxylic acid is thus obtained in the form of a yellow solid melting at 204° C.

Workup

  1. temperatureis then refluxed for 2 hours
  2. concentrationThe reaction medium is then concentrated to dryness under reduced pressure (2.7 kPa)
  3. additionis added 0.17 g of citric acid
  4. extractionThe mixture is extracted with twice 50 cm3 of dichloromethane, and acidification of the aqueous phase
  5. additionis continued by addition of citric acid down to pH 2
  6. extractionthe extraction
  7. customdried
  8. customevaporated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-19347d38af144b1cbe1f80ec4d85d7a8
Source dataset
uspto-grants-2011_02
Patent number
US07884123B2

Reaction notes

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