Hydrochloric Acid → HCID 23336006, compound

HRID 437728Notes

Reaction equation

HRID 437728 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4]([CH3:7])[C:3]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[CH3:13][N:14]=[C:15]=[O:16].Cl>N1C=CC=CC=1>[CH2:11]([O:10][C:8]([C:3]1[C:4]([CH3:7])=[N:5][S:6][C:2]=1[NH:1][C:15]([NH:14][CH3:13])=[O:16])=[O:9])[CH3:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 12228Methyl IsocyanateHCID 2820511ethyl 5-amino-3-methylisothiazole-4-carboxylate

Product 1

HCID 23336006HCID 23336006, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 5-amino-4-ethoxycarbonyl-3-methylisothiazole (prepared by the method of Goerdeler and Horn, op cit; 3.72 g.) in pyridine (10 ml.) was treated at 80° C. with methyl isocyanate (1.5 ml.) and the mixture was maintained at 80° C. for 6 hours. The mixture was then poured into an excess of dilute aqueous hydrochloric acid to give an off-white precipitate which was filtered off and recrystallised from ethanol to give colourless crystals of 1-(4-ethoxycarbonyl-3-methylisothiazol-5-yl)-3-methylurea (1.6 g.), m.p. 191°-193° C.

Workup

  1. customto give an off-white precipitate which
  2. filtrationwas filtered off
  3. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-0224fe3a24b54ea69e351b98e9e2d980
Source dataset
uspto-grants-1977_06
Patent number
US04032323

Reaction notes

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