Hydrogen Bromide → 2-(Dimethylamino)benzo[d]oxazol-5-ol

HRID 706232Notes

Reaction equation

HRID 706232 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([N:11]([CH3:13])[CH3:12])=[N:8][C:7]=2[CH:14]=1.Br>[Br-].C([P+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+]>[CH3:12][N:11]([CH3:13])[C:9]1[O:10][C:6]2[CH:5]=[CH:4][C:3]([OH:2])=[CH:14][C:7]=2[N:8]=1

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 57344577(5-Methoxy-benzooxazol-2-yl)-dimethyl-amine

Product 1

HCID 671102512-(Dimethylamino)benzo[d]oxazol-5-olYield 92.4%

Reagents, catalysts & solvents 2

HCID 76564Tetrabutylphosphonium bromideCatalystHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of (5-methoxy-benzooxazol-2-yl)-dimethyl-amine (6.41 g, 0.03 mol), tetrabutylphosphonium bromide (1.13 g, 3.34 mmol), and 48% HBr (40 mL) was stirred at 105° C. for twenty-five hours before it was cooled to room temperature, neutralized with 10N NaOH (30 mL) to pH=8. The resulting precipitate was filtered, washed with water, and dried in vacuo to give the title compound as a pale brown solid (4.94 g): 1H NMR (CDCl3, 200 MHz): δ=7.05 (m, 1H), 6.86 (m, 1H), 6.48 (m, 1H), 3.19 (s, 6H).

Workup

  1. temperaturewas cooled to room temperature
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-d40b9df7168545779d76ea96a311c7fa
Source dataset
uspto-grants-2015_11
Patent number
US09174976B2

Reaction notes

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