Hydrochloric Acid → HCID 70055756, compound

HRID 1977281Notes

Reaction equation

HRID 1977281 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[S:17][C:16]([C:18]4[CH:27]=[CH:26][C:21]([C:22]([O:24]C)=[O:23])=[CH:20][CH:19]=4)=[N:15][N:14]=3)=[CH:9][N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O1CCCC1.[OH-].[Na+].[ClH:35]>O.C(O)C>[ClH:35].[N:1]1([C:7]2[N:8]=[CH:9][C:10]([C:13]3[S:17][C:16]([C:18]4[CH:27]=[CH:26][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=4)=[N:15][N:14]=3)=[CH:11][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21997562HCID 21997562, compound

Product 1

HCID 70055756HCID 70055756, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a refluxing suspension of methyl 4-[5-[2-(1-piperidyl) pyridin-5-yl]-1,3,4-thiadiazol-2-yl]benzoate (1.50 g) in a mixed solvent of tetrahydrofuran (75 ml) and ethanol (15 ml) was added dropwise 10% sodium hydroxide aqueous solution (3.15 ml). The mixture was refluxed for 1.5 hours and cooled to ambient temperature. To the reaction mixture was added water (100 ml) and the pH was adjusted to 1 with 1N hydrochloric acid (15 ml). The mixture was stirred for 30 minutes at ambient temperature and the resulting precipitates were filtered, washed with water and dried to give 4-[5-[6-(1-piperidyl) pyridin-3-yl]-1,3,4-thiadiazol-2-yl]benzoic acid hydrochloride (1.36 g), as a yellow solid.

Workup

  1. temperatureThe mixture was refluxed for 1.5 hours
  2. customthe resulting precipitates
  3. filtrationwere filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-090ba23cfe23491c8aab52ada75c1469
Source dataset
uspto-grants-2001_05
Patent number
US06232290B1

Reaction notes

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