Sulfuric Acid → 3-Methoxyisothiazole-4-carboxamide

HRID 1862986Notes

Reaction equation

HRID 1862986 reaction equation
[C:1]([C:3]1[C:4]([O:8][CH3:9])=[N:5][S:6][CH:7]=1)#[N:2].S(=O)(=O)(O)[OH:11]>>[C:1]([C:3]1[C:4]([O:8][CH3:9])=[N:5][S:6][CH:7]=1)(=[O:11])[NH2:2]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 123939363-Methoxy-1,2-thiazole-4-carbonitrile

Product 1

HCID 123939413-Methoxyisothiazole-4-carboxamide

Procedure

A solution of 2.8 g. (0.02 mole) of 4-cyano-3-methoxyisothiazole prepared as in Example 18 in 30 ml. of 75% sulfuric acid was heated at 70° C. for 0.5 hour. The solution was then cooled and poured into ice to give after filtration and drying 0.95 g. of 4-carbamoyl-3-methoxyisothiazole, m.p. 165°-168° C. By continuous ether extraction of the aqueous filtrate an addition 1.13 g. of 4-carbamoyl-3-methoxyisothiazole was obtained to give a total yield of 2.08 g. (66%).

Workup

  1. temperatureThe solution was then cooled
  2. additionpoured into ice
  3. customto give
  4. filtrationafter filtration
  5. customdrying 0.95 g
  6. extractionBy continuous ether extraction of the aqueous filtrate
  7. additionan addition 1.13 g

Sources & evidence

ORD record
ord-0be228504f3f408b96bb608aed44db44
Source dataset
uspto-grants-1979_09
Patent number
US04167575

Reaction notes

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