Hydrochloric Acid → HCID 22494600, compound

HRID 351556Notes

Reaction equation

HRID 351556 reaction equation
FC(F)(F)C(O)=O.C([O:10][C:11](=[O:38])[C:12]1[CH:17]=[CH:16][C:15]([C:18]2[N:19]=[C:20]3[N:24]([CH:25]=2)[N:23]=[C:22]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[CH:28][CH:27]=2)[S:21]3)=[CH:14][CH:13]=1)C.CO.[OH-].[Na+].Cl>O1CCCC1>[CH2:33]([O:32][C:29]1[CH:28]=[CH:27][C:26]([C:22]2[S:21][C:20]3=[N:19][C:18]([C:15]4[CH:14]=[CH:13][C:12]([C:11]([OH:38])=[O:10])=[CH:17][CH:16]=4)=[CH:25][N:24]3[N:23]=2)=[CH:31][CH:30]=1)[CH2:34][CH2:35][CH2:36][CH3:37]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 69817681HCID 69817681, compound

Product 1

HCID 22494600HCID 22494600, compoundYield 110.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[2-(4-pentyloxyphenyl)imidazo-[2,1-b][1,3,4]thiadiazol-6-yl]benzoic acid ethyl ester trifluoroacetic acid salt (5.2 g) in the mixture of methanol (104 ml) and tetrahydrofuran (52 ml) was added 2N NaOH aq. (47 ml) and refluxed for 36 hours. The reaction mixture was adjusted to pH 1-2 with 1N HCl and the resulting precipitate was collected by filtration to give 4-[2-(4-pentyloxyphenyl)-imidazo[2,1-b][1,3,4]thiadiazol-6-yl]benzoic acid (4.27 g).

Workup

  1. temperaturerefluxed for 36 hours
  2. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-821dbe5df7014d25a15b753e56479118
Source dataset
uspto-grants-2004_06
Patent number
US06743776B2

Reaction notes

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