Methyl Isocyanate → HCID 20367573, compound

HRID 616500Notes

Reaction equation

HRID 616500 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4]([N:7]([CH2:10][CH3:11])[CH2:8][CH3:9])[C:3]=1[C:12]#[N:13].[CH3:14][N:15]=[C:16]=[O:17]>C([O-])(=O)C.C([O-])(=O)C.C([Sn+2]CCCC)CCC.O1CCCC1>[CH3:14][NH:15][C:16]([NH:1][C:2]1[S:6][N:5]=[C:4]([N:7]([CH2:8][CH3:9])[CH2:10][CH3:11])[C:3]=1[C:12]#[N:13])=[O:17]

Participants

5

Reactant 2

HCID 12228Methyl IsocyanateHCID 203675925-Amino-3-(diethylamino)-1,2-thiazole-4-carbonitrile

Product 1

HCID 20367573HCID 20367573, compound

Reagents, catalysts & solvents 2

HCID 9798523Di-n-butyl diacetoxy tinCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 9.8 g of 5-amino-4-cyano-3-(diethylamino)isothiazole, 20 drops of dibutyltin diacetate, and about 15 ml of methyl isocyanate in 50 ml of dry tetrahydrofuran was heated under reflux for 21 hours, at which time thin-layer chromatographic analysis indicated reaction to be complete. The solution was concentrated under reduced pressure and the residue was recrystallized from ethanol to give 11.7 g of white 1-methyl-3-(4-cyano-3-(diethylamino)-5-isothiazolyl)urea, m.p. 182°-183°. The nmr spectrum was consistent with the assigned structure.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 21 hours, at which time thin-layer chromatographic analysis
  3. customreaction
  4. concentrationThe solution was concentrated under reduced pressure
  5. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-38aa91c7d12046d49f2a03e1b9f3b43b
Source dataset
uspto-grants-1978_02
Patent number
US04075001

Reaction notes

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