Water → HCID 21426788, compound

HRID 437729Notes

Reaction equation

HRID 437729 reaction equation
[CH2:1]([NH2:3])[CH3:2].[CH2:4]([O:6][C:7]([C:9]1[C:10]([CH3:24])=[N:11][S:12][C:13]=1[NH:14][C:15](OC1C=CC=CC=1)=[O:16])=[O:8])[CH3:5].O>C(O)C>[CH2:1]([NH:3][C:15](=[O:16])[NH:14][C:13]1[S:12][N:11]=[C:10]([CH3:24])[C:9]=1[C:7]([O:6][CH2:4][CH3:5])=[O:8])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 6341EthylamineHCID 2820507HCID 2820507, compound

Product 1

HCID 21426788HCID 21426788, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A 50% w/v solution of ethylamine in ethanol (30 ml.) was added to a solution of 4-ethoxycarbonyl-3-methyl-5-phenoxycarbonylaminoisothiazole (prepared according to the method of Goerdeler and Horn, Chemische Berichte, 1963, 96, 1551; 30.6 g.) in warm ethanol (120 ml.). The mixture was then heated under reflux for 1 minute, and allowed to cool to ambient temperature and stand for 2 days. The mixture was then heated under reflux for 5 minutes, allowed to cool to ambient temperature and stand for 1 day and poured into cold water (1 liter). The precipitated solid was filtered off, dried and recrystallised from benzene (300 ml.) to give 3-ethyl-1-(4-ethoxycarbonyl-3-methylisothiazol-5-yl)urea (24.8 g.), m.p. 141° C.

Workup

  1. customprepared
  2. temperatureThe mixture was then heated
  3. temperatureunder reflux for 1 minute
  4. temperatureThe mixture was then heated
  5. temperatureunder reflux for 5 minutes
  6. temperatureto cool to ambient temperature
  7. waitstand for 1 day
  8. filtrationThe precipitated solid was filtered off
  9. customdried
  10. customrecrystallised from benzene (300 ml.)

Sources & evidence

ORD record
ord-f6c7dd87132645749f3be9a7132f7e13
Source dataset
uspto-grants-1977_06
Patent number
US04032323

Reaction notes

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