Sulfuric Acid → HCID 18550659, compound

HRID 1439321Notes

Reaction equation

HRID 1439321 reaction equation
[CH3:1][NH:2][C:3]([NH:5][C:6]1[S:10][N:9]=[C:8]([O: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]([O:11][CH2:12][CH3:13])[C:7]=1[C:14](=[O:17])[NH2:15])=[O:4]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 21396821HCID 21396821, compound

Product 1

HCID 18550659HCID 18550659, compound

Procedure

A solution of 5.6 g of 1-methyl-3-(4-cyano-3-ethoxy-5-isothiazolyl)urea (from Example I) in 10 ml of concentrated sulfuric acid was heated at 50° during 1.5 hours. The reaction mixture was poured into 200 ml of ice-water and stirred for one half hour. The resultant precipitate was collected by filtration and was allowed to air-dry overnight. The solid was slurried with 50 ml of saturated sodium bicarbonate solution. The resulting white solid was collected by filtration and recrystallized from ethanol to give 4.3 g of 1-methyl-3-(4-carbamoyl-3-ethoxy-5-isothiazolyl)urea, m.p. 240°-241°.

Workup

  1. filtrationThe resultant precipitate was collected by filtration
  2. customto air-dry overnight
  3. filtrationThe resulting white solid was collected by filtration
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-fc2b95c3498d41aeb9b5f0c899654b34
Source dataset
uspto-grants-1977_11
Patent number
US04059433

Reaction notes

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