Sulfuric Acid → HCID 21399278, compound

HRID 1438860Notes

Reaction equation

HRID 1438860 reaction equation
[CH3:1][NH:2][C:3]([NH:5][C:6]1[S:10][N:9]=[C:8]([S:11]([CH2:14][CH3:15])(=[O:13])=[O:12])[C:7]=1[C:16]#[N:17])=[O:4].S(=O)(=O)(O)[OH:19]>>[CH3:1][NH:2][C:3]([NH:5][C:6]1[S:10][N:9]=[C:8]([S:11]([CH2:14][CH3:15])(=[O:13])=[O:12])[C:7]=1[C:16](=[O:19])[NH2:17])=[O:4]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 21399282HCID 21399282, compound

Product 1

HCID 21399278HCID 21399278, compound

Procedure

A mixture of 8.8 g of 1-methyl-3-(4-cyano-3-(ethylsulfonyl) -5-isothiazolyl)urea and 10 ml of concentrated sulfuric acid was heated at 100° for 2.25 hours, then poured into 150 ml of ice-water. The solid was isolated and recrystallized from acetic acid-water to give 2.8 g of 1-methyl-3-(4-carbamoyl-3-(ethylsulfonyl)-5-isothiazolyl)urea, m.p. 219°-220°. An additional 2.2 g was obtained by concentrating the mother liquor from the recrystallization. The nmr and ir spectra were consistent with the assigned structure.

Workup

  1. temperaturewas heated at 100° for 2.25 hours
  2. customThe solid was isolated
  3. customrecrystallized from acetic acid-water

Sources & evidence

ORD record
ord-a967aab857474869a5a7bb89a5ea562f
Source dataset
uspto-grants-1977_11
Patent number
US04057416

Reaction notes

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