Hydrochloric Acid → Methyl 2-chloro-4-methylbenzo[d]thiazole-5-carboxylate

HRID 1263408Notes

Reaction equation

HRID 1263408 reaction equation
N([O-])=O.[Na+].N[C:6]1[S:7][C:8]2[CH:14]=[CH:13][C:12]([C:15]([O:17][CH3:18])=[O:16])=[C:11]([CH3:19])[C:9]=2[N:10]=1.[ClH:20]>O.P(=O)(O)(O)O.Cl[Cu]>[Cl:20][C:6]1[S:7][C:8]2[CH:14]=[CH:13][C:12]([C:15]([O:17][CH3:18])=[O:16])=[C:11]([CH3:19])[C:9]=2[N:10]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 22390084Methyl 2-amino-4-methylbenzo[d]thiazole-5-carboxylateHCID 23668193Sodium Nitrite

Product 1

HCID 22390080Methyl 2-chloro-4-methylbenzo[d]thiazole-5-carboxylate

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 962WaterSolventHCID 1004Phosphoric AcidSolvent

Conditions

Temperature
100 °C

Procedure

At −8° C., a solution of 9.3 g of NaNO2 (0.14 mol) in 10 ml of water was added dropwise to a solution of 5 g of methyl 2-amino-4-methylbenzothiazole-5-carboxylate (0.02 mol) in 150 ml of phosphoric acid. At 5° C., a solution of 3 g of CuCl and 12 ml of conc. HCl was then added dropwise. The reaction mixture was heated to 100° C. After cooling, the residue was filtered off with suction, washed with water and dried. The product was purified by silica gel column chromatography.

Workup

  1. temperatureAfter cooling
  2. filtrationthe residue was filtered off with suction
  3. washwashed with water
  4. customdried
  5. customThe product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-542ff47eaa354c54800ee6ac1c4abec1
Source dataset
uspto-grants-2003_04
Patent number
US06541423B1

Reaction notes

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