2-Amino-4-methylbenzothiazole → 4-Methylbenzo[d]thiazol-2-ol

HRID 469314

Reaction equation

HRID 469314 reaction equation
N[C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:5]=2[N:6]=1.N([O-])=[O:13].[Na+]>C(O)=O.C(O)(=O)C.Cl.O>[CH3:11][C:7]1[C:5]2[NH:6][C:2](=[O:13])[S:3][C:4]=2[CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 2

HCID 151322-Amino-4-methylbenzothiazoleHCID 23668193Sodium Nitrite

Product 1

HCID 127708804-Methylbenzo[d]thiazol-2-ol

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 284Formic AcidSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

5.00 g (30.5 mmol) 2-amino-4-methylbenzothiazole in 15.0 mL formic acid, 6.10 mL glacial acetic acid and 112 mL conc. hydrochloric acid were cooled to −5° C. with stirring and slowly combined with a solution of 2.10 g (30.5 mmol) sodium nitrite in 5.0 mL water. The reaction mixture was stirred for 20 min at this temperature, then heated to RT and then refluxed overnight. The cooled mixture was then mixed with water and extracted several times with EtOAc. The combined organic phases were washed with saturated sodium chloride solution, dried on sodium sulphate, filtered and the filtrate was evaporated down.

Workup

  1. stirringThe reaction mixture was stirred for 20 min at this temperature
  2. temperaturerefluxed overnight
  3. extractionextracted several times with EtOAc
  4. washThe combined organic phases were washed with saturated sodium chloride solution
  5. customdried on sodium sulphate
  6. filtrationfiltered
  7. customthe filtrate was evaporated down

Sources & evidence

ORD record
ord-d83cbdc43ff5451f910282499503eb4e
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Linked notes

Loading…