Hydrochloric Acid → 4-[2-(4-Butyloxyphenyl)imidazo[2,1-b][1,3,4]thiadiazol-6-yl]benzoic acid

HRID 1977269Notes

Reaction equation

HRID 1977269 reaction equation
FC(F)(F)C(O)=O.C([O:10][C:11](=[O:37])[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][CH3:36])=[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:16]=[CH:17][C:12]([C:11]([OH:37])=[O:10])=[CH:13][CH:14]=4)=[CH:25][N:24]3[N:23]=2)=[CH:31][CH:30]=1)[CH2:34][CH2:35][CH3:36]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 70053552HCID 70053552, compound

Product 1

HCID 219974614-[2-(4-Butyloxyphenyl)imidazo[2,1-b][1,3,4]thiadiazol-6-yl]benzoic acidYield 102.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[2-(4-butyloxyphenyl)imidazo[2,1-b]-[1,3,4]thiadiazol-6-yl]benzoic acid ethyl ester trifluoroacetic acid salt (2.05 g) in the mixture of methanol (41 ml) and tetrahydrofuran (20.5 ml) was added 2N NaOH aq. (19.1 ml) and refluxed for 17 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-butyloxyphenyl)imidazo[2,1-b][1,3,4]thiadiazol-6-yl]benzoic acid (1.544 g).

Workup

  1. temperaturerefluxed for 17 hours
  2. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-649f15571e004aa4a176d5ae8db67358
Source dataset
uspto-grants-2001_05
Patent number
US06232290B1

Reaction notes

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