Sodium Hydroxide → 6-Hydroxybenzothiazole

HRID 22703

Reaction equation

HRID 22703 reaction equation
N[C:2]1[CH:10]=[CH:9][C:5]2[N:6]=[CH:7][S:8][C:4]=2[CH:3]=1.N([O-])=[O:12].[Na+].[OH-].[Na+]>O.OS(O)(=O)=O>[S:8]1[C:4]2[CH:3]=[C:2]([OH:12])[CH:10]=[CH:9][C:5]=2[N:6]=[CH:7]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 682886-AminobenzothiazoleHCID 23668193Sodium Nitrite

Product 1

HCID 1518116-Hydroxybenzothiazole

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
160 °C

Procedure

To a solution of 6-aminobenzothiazole (1.0 g, 6.66 mmol) in water (22 mL) and H2SO4 (16 mL) at 5° C. was added a solution of sodium nitrite (460 mg, 6.72 mmol) in water (13 mL) keeping the temperature below 5° C. The resulting solution was allowed to stir for 15 minutes. The reaction mixture was heated to 160° C. and a solution of H2SO4 (50 mL) and water (38 mL) was slowly added. The resulting mixture was allowed to stir for 1 h. The mixture was allowed to cool and an aqueous solution of 50% sodium hydroxide was added until the pH=7. The mixture was extracted with ethyl acetate and washed with brine. The combined organic was dried over MgSO4 and evaporated to yield a semi-solid. The semi-solid was purified by column chromatography (40% ethyl acetate/hexanes) to yield benzothiazo-6-ol 16 as an off-white solid. Synthesis of 6-(oxiran-2-ylmethoxy)benzothiazole (48):

Workup

  1. customthe temperature below 5° C
  2. stirringto stir for 1 h
  3. temperatureto cool
  4. extractionThe mixture was extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialThe combined organic was dried over MgSO4
  7. customevaporated
  8. customto yield a semi-solid
  9. customThe semi-solid was purified by column chromatography (40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-1207b74cfa9b4156ad1030636a632b67
Source dataset
uspto-grants-2005_02
Patent number
US06849632B2

Linked notes

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