Hydrogen Bromide → HCID 6625430, compound

HRID 409309Notes

Reaction equation

HRID 409309 reaction equation
C[O:2][C:3]1[CH:17]=[CH:16][C:6]2[N:7]=[C:8]([N:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[S:9][C:5]=2[CH:4]=1.Br>[Br-].C([P+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+]>[N:10]1([C:8]2[S:9][C:5]3[CH:4]=[C:3]([OH:2])[CH:17]=[CH:16][C:6]=3[N:7]=2)[CH2:11][CH2:12][O:13][CH2:14][CH2:15]1

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 7110122HCID 7110122, compound

Product 1

HCID 6625430HCID 6625430, compoundYield 92.9%

Reagents, catalysts & solvents 2

HCID 76564Tetrabutylphosphonium bromideCatalystHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6-methoxy-2-morpholin-4-yl-benzothiazole (12.20 g, 48.7 mmol), tetrabutylphosphonium bromide (1.65 g, 4.87 mmol) and 48% HBr (80 mL) was stirred at 100° C. for twenty hours before it was cooled to room temperature, neutralized with 10N NaOH (60 mL) to pH=5-6. The mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, concentrated in vacuo to give the title compound as a white solid (10.69 g): 1H NMR (CDCl3, 200 MHz): δ=7.28 (m, 1H), 7.15 (m, 1H), 6.75 (m, 1H), 3.70 (m, 4H), 3.43 (m, 4H).

Workup

  1. temperaturewas cooled to room temperature
  2. extractionThe mixture was extracted with dichloromethane
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-16c563f7a99b4e1699d83abe5dd10d75
Source dataset
uspto-grants-2014_06
Patent number
US08759373B2

Reaction notes

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