p-Toluenesulfonic acid monohydrate → 5-Methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine p-toluenesulfonic acid salt

HRID 1361446Notes

Reaction equation

HRID 1361446 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]2[N:8]=[CH:9][S:10][C:4]=2[CH2:3]1.O.[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18]([OH:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1>CC(O)C>[C:12]1([CH3:22])[CH:13]=[CH:14][C:15]([S:18]([OH:21])(=[O:19])=[O:20])=[CH:16][CH:17]=1.[CH3:1][N:2]1[CH2:7][CH2:6][C:5]2[N:8]=[CH:9][S:10][C:4]=2[CH2:3]1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 111864405-Methyl-4,5,6,7-tetrahydrothiazolo(5,4-c)pyridine

Product 1

HCID 111864395-Methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine p-toluenesulfonic acid saltYield 90.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

5-Methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine (1.00 g) was dissolved in 2-propanol (10 mL) at room temperature, and p-toluenesulfonic acid monohydrate (1.23 g) was added thereto at room temperature, followed by stirring at room temperature for 20 minutes. When the resultant mixture was cooled to 0° C., a salt was crystallized out of the mixture. After the resultant mixture was stirred at 0° C. for 2 hours, the precipitated salt was collected by filtration, and was washed with 2-propanol (2 mmol). The wet material was dried at room temperature under reduced pressure, to thereby give 1.91 g of the title compound.

Workup

  1. customat room temperature
  2. customa salt was crystallized out of the mixture
  3. stirringAfter the resultant mixture was stirred at 0° C. for 2 hours
  4. filtrationthe precipitated salt was collected by filtration
  5. customThe wet material was dried at room temperature under reduced pressure

Sources & evidence

ORD record
ord-a9fe379da6ca4b219e5e5fffac3c4f88
Source dataset
uspto-grants-2011_02
Patent number
US07880005B2

Reaction notes

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