Sulfuric Acid → HCID 54174205, compound

HRID 616516Notes

Reaction equation

HRID 616516 reaction equation
[CH3:1][NH:2][C:3]([NH:5][C:6]1[S:10][N:9]=[C:8]([N:11]([CH2:13][CH3:14])[CH3:12])[C:7]=1[C:15]#[N:16])=[O:4].S(=O)(=O)(O)[OH:18].S1C=CC(NC(N)=O)=N1.[OH-].[NH4+]>>[CH3:1][NH:2][C:3]([NH:5][C:6]1[S:10][N:9]=[C:8]([N:11]([CH2:13][CH3:14])[CH3:12])[C:7]=1[C:15](=[O:18])[NH2:16])=[O:4]

Participants

5

Reactant 4

HCID 1118Sulfuric Acid2×HCID 14923Ammonium HydroxideHCID 20367572HCID 20367572, compoundHCID 54329983HCID 54329983, compound

Product 1

HCID 54174205HCID 54174205, compound

Procedure

A mixture of 6.8 g of 1-methyl-3-(4-cyano-3-(ethylmethylamino)-5-isothiazolyl)urea and 20 ml of concentrated sulfuric acid was prepared by addition of small portions of the isothiazolylurea to the rapidly stirred sulfuric acid during a 15 minute period at ambient temperature. Stirring of the mixture was continued until a homogeneous solution was obtained. The solution was heated at 50° in a thermostated water bath for 1 hour. The reaction mixture was poured into 200 ml of ice-water and the resulting slurry was made strongly basic (pH 14) by addition of concentrated ammonium hydroxide. The temperature was maintained at 0° by addition of the ice during the pH adjustment process. The solid was collected by filtration and the filter cake dried. The solid was recrystallized from ethyl acetate to yield 4.4 g of 1-methyl-3-(4-carbamoyl-3-(ethylmethylamino)-5-isothiazolyl)urea, mp 165°-168°. The ir and nmr spectra were consistent with the assigned structure.

Workup

  1. customwas obtained
  2. temperatureThe solution was heated at 50° in a thermostated water bath for 1 hour
  3. filtrationThe solid was collected by filtration
  4. customthe filter cake dried
  5. customThe solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-f5cee3ae10df405a9c3858909ecf1924
Source dataset
uspto-grants-1978_02
Patent number
US04075001

Reaction notes

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