Sodium Bicarbonate → 2-Methylbenzo[d]thiazol-7-ol

HRID 366431Notes

Reaction equation

HRID 366431 reaction equation
C[O:2][C:3]1[C:11]2[S:10][C:9]([CH3:12])=[N:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.Cl.N1C=CC=CC=1.C([O-])(O)=O.[Na+]>O>[CH3:12][C:9]1[S:10][C:11]2[C:3]([OH:2])=[CH:4][CH:5]=[CH:6][C:7]=2[N:8]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 10176127Pyridinium chlorideHCID 164432667-Methoxy-2-methylbenzo[d]thiazole

Product 1

HCID 232893082-Methylbenzo[d]thiazol-7-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
165 °C

Procedure

7-Methoxy-2-methyl-benzothiazole (400 mg, 2.23 mmol) was mechanically mixed with solid pyridine hydrochloride (6.00 g, 52 mmol) and then heated to 160-170° C. in a sealed vessel for 16 hours. Water (40 mL) was added to the warm mixture, the pH was adjusted to neutrality with NaHCO3 and the mixture was extracted with 1:1 CHCl2 /CHCl3 (4×10 mL). The pooled organic extracts were dried over MgSO4, filtered, and concentrated in vacuo to provide 2-methyl-benzothiazol-7-ol as a waxy yellow solid. (260 mg; GC-MS m/z 165).

Workup

  1. extractionthe mixture was extracted with 1:1 CHCl2 /CHCl3 (4×10 mL)
  2. dry with materialThe pooled organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9805bf17eb8f43b9bb7b95cbd759c47d
Source dataset
uspto-grants-2000_10
Patent number
US06130217

Reaction notes

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