Water → 6-Hydroxybenzothiazole

HRID 563885Notes

Reaction equation

HRID 563885 reaction equation
C[O:2][C:3]1[CH:11]=[CH:10][C:6]2[N:7]=[CH:8][S:9][C:5]=2[CH:4]=1.O.C(=O)([O-])O.[Na+]>Br>[OH:2][C:3]1[CH:11]=[CH:10][C:6]2[N:7]=[CH:8][S:9][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3501866-MethoxybenzothiazoleHCID 516892Sodium Bicarbonate

Product 1

HCID 1518116-HydroxybenzothiazoleYield 95.6%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

The product of Step 1 (1.2 g) in hydrobromic acid (10 ml, 48%) was heated at 120° C. with stirring for 6 hours then stored at ambient temperature for 2 days. The hot, pale yellow solution produced a suspension on cooling. The suspension was dissolved by the addition of water then the solution was adjusted to pH 6 by addition of sodium hydrogen carbonate and the solid that precipitated was filtered from solution, washed with water and sucked to dryness. The solid was dissolved in ethyl acetate, the solution dried over magnesium sulphate and evaporated to give 6-hydroxybenzothiazole as a colourless solid (1.05 g).

Workup

  1. waitthen stored at ambient temperature for 2 days
  2. customThe hot, pale yellow solution produced a suspension
  3. temperatureon cooling
  4. customthe solid that precipitated
  5. filtrationwas filtered from solution
  6. washwashed with water
  7. dissolutionThe solid was dissolved in ethyl acetate
  8. dry with materialthe solution dried over magnesium sulphate
  9. customevaporated

Sources & evidence

ORD record
ord-7c12012246d546498362c83cbfcf61a0
Source dataset
uspto-grants-2011_11
Patent number
US08067592B2

Reaction notes

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