Hydrochloric Acid → HCID 21997468, compound

HRID 1977263Notes

Reaction equation

HRID 1977263 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[S:20][C:19]([C:21]3[CH:30]=[CH:29][C:24]([C:25]([O:27]C)=[O:26])=[CH:23][CH:22]=3)=[N:18][N:17]=2)=[CH:12][CH:11]=1.[OH-].[Na+].Cl>O.O1CCCC1.CO>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[S:20][C:19]([C:21]3[CH:22]=[CH:23][C:24]([C:25]([OH:27])=[O:26])=[CH:29][CH:30]=3)=[N:18][N:17]=2)=[CH:14][CH:15]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21997544HCID 21997544, compound

Product 1

HCID 21997468HCID 21997468, compoundYield 96.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 4-[5-[4-(6-methoxy-n-hexyloxy)-phenyl]-1,3,4-thiadiazol-2-yl]benzoate (179.6 g), sodium hydroxide (25.3 g), water (250 ml), methanol (1 L), and tetrahydrofuran (750 ml) was heated under refluxing for 1 hour then cooled to room temperature and poured into water (7 L). The pH of the stirred mixture was adjusted to 2.0 with 6N-hydrochloric acid and the precipitate collected by filtration, washed thoroughly with water, followed by acetonitrile, then dried under hi-vacuum at 50° C. to give 4-[5-[4-(6-methoxy-n-hexyloxy)phenyl]-1,3,4-thiadiazol-2-yl]benzoic acid (167 g) as a yellow powder.

Workup

  1. temperaturewas heated
  2. temperatureunder refluxing for 1 hour
  3. filtrationthe precipitate collected by filtration
  4. washwashed thoroughly with water
  5. customdried under hi-vacuum at 50° C.

Sources & evidence

ORD record
ord-ac22c16c3a36426eaed5a196970fccb4
Source dataset
uspto-grants-2001_05
Patent number
US06232290B1

Reaction notes

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