Sulfuric Acid → HCID 18550614, compound

HRID 1438857Notes

Reaction equation

HRID 1438857 reaction equation
[CH3:1][NH:2][C:3]([NH:5][C:6]1[S:10][N:9]=[C:8]([S:11][CH2:12][CH3:13])[C:7]=1[C:14]#[N:15])=[O:4].S(=O)(=O)(O)[OH:17]>>[CH3:1][NH:2][C:3]([NH:5][C:6]1[S:10][N:9]=[C:8]([S:11][CH2:12][CH3:13])[C:7]=1[C:14](=[O:17])[NH2:15])=[O:4]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 21399269HCID 21399269, compound

Product 1

HCID 18550614HCID 18550614, compound

Procedure

A stirred solution of 4.0 g of 1-methyl-3-(4-cyano-3-(ethylthio)-5-isothiazolyl)urea in 6 ml of concentrated sulfuric acid was heated at 160° for 1.5 hours. After this time the reaction mixture was poured into 120 ml of ice-water, and this mixture was stirred for 45 minutes. The white precipitate was collected by filtration. The solid was recrystallized from ethanol to give 4.0 grams of 1-methyl-3-(4-carbamoyl-3-(ethylthio)-5-isothiazolyl)urea, m.p. 205°. The nmr spectra was consistent with the assigned structure.

Workup

  1. filtrationThe white precipitate was collected by filtration
  2. customThe solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-ee08a3d5e222469e8207e2b4706e0d21
Source dataset
uspto-grants-1977_11
Patent number
US04057416

Reaction notes

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