p-Toluenesulfonic acid monohydrate → 2-Bromo-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine 4-methylbenzenesulfonate

HRID 557241Notes

Reaction equation

HRID 557241 reaction equation
[Br:1][C:2]1[S:3][C:4]2[CH2:5][N:6]([CH3:11])[CH2:7][CH2:8][C:9]=2[N:10]=1.O.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19]([OH:22])(=[O:21])=[O:20])=[CH:15][CH:14]=1>CO>[C:13]1([CH3:23])[CH:14]=[CH:15][C:16]([S:19]([OH:22])(=[O:20])=[O:21])=[CH:17][CH:18]=1.[Br:1][C:2]1[S:3][C:4]2[CH2:5][N:6]([CH3:11])[CH2:7][CH2:8][C:9]=2[N:10]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 111723352-Bromo-5-methyl-4,5,6,7-tetrahydrothiazolo(5,4-c)pyridine

Product 1

HCID 112118752-Bromo-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine 4-methylbenzenesulfonateYield 87.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

2-Bromo-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine (557.6 g) was dissolved in methanol (3.9 L), and to the solution was added dropwise a solution of p-toluenesulfonic acid monohydrate (500.0 g) in methanol (1.7 L) at 30° C. The resultant mixture was stirred at the same temperature for 1 hour, and then at or below 10° C. for 2 hours. The precipitated crystals were collected by filtration, and were washed with methanol (1.1 L), followed by drying at 40° C. under reduced pressure, to thereby give 851.9 g of the title compound.

Workup

  1. filtrationThe precipitated crystals were collected by filtration
  2. washwere washed with methanol (1.1 L)
  3. customby drying at 40° C. under reduced pressure

Sources & evidence

ORD record
ord-f97d4e12307341469aaa0f9a8f8342b5
Source dataset
uspto-grants-2011_11
Patent number
US08058440B2

Reaction notes

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