Sulfuric Acid → 3-Methoxy-1,2-thiazole-4-carboxylic acid

HRID 972506Notes

Reaction equation

HRID 972506 reaction equation
[C:1]([C:4]1[C:5]([O:9][CH3:10])=[N:6][S:7][CH:8]=1)(=[O:3])N.S(=O)(=O)(O)[OH:12].N([O-])=O.[Na+]>O>[C:1]([C:4]1[C:5]([O:9][CH3:10])=[N:6][S:7][CH:8]=1)([OH:12])=[O:3]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 123939413-Methoxyisothiazole-4-carboxamideHCID 23668193Sodium Nitrite

Product 1

HCID 123939393-Methoxy-1,2-thiazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 7.9 g. (0.05 mole) of 4-carbamoyl-3-methoxyisothiazole prepared as in Example 19 in 90 ml. of 80% sulfuric acid at 10°-15° C. was added slowly beneath the surface of the liquid a solution of 9.5 g. (0.137 mole) of sodium nitrite in 13 ml. of H2O. When addition was complete the solution was allowed to come to 25° C., and then was heated to 60° C., for several minutes. After cooling to 25° C. the reaction solution was poured onto ice to precipitate 3.64 g. (46%) of 4-carboxy-3-methoxyisothiazole as a white solid, m.p. 182°-185° C.

Workup

  1. additionWhen addition
  2. customto come to 25° C.
  3. temperatureAfter cooling to 25° C. the reaction solution
  4. additionwas poured onto ice
  5. customto precipitate 3.64 g

Sources & evidence

ORD record
ord-bb5cab71d7844d708a6462e1a4d9ad8f
Source dataset
uspto-grants-1977_10
Patent number
US04053479

Reaction notes

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