Methyl Isocyanate → HCID 178485914, compound

HRID 2397171Notes

Reaction equation

HRID 2397171 reaction equation
[CH3:1][NH:2][C:3]1[S:4][C:5]([SH:8])=[N:6][N:7]=1.[CH3:9][N:10]=[C:11]=[O:12]>O1CCOCC1.C(N(CC)CC)C>[CH3:9][NH:10][C:11]([N:2]([CH3:1])[C:3]1[S:4][C:5]([SH:8])=[N:6][N:7]=1)=[O:12]

Participants

5

Reactant 2

HCID 12228Methyl IsocyanateHCID 178482505HCID 178482505, compound

Product 1

HCID 178485914HCID 178485914, compoundYield 75.5%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneCatalystHCID 8471TriethylamineSolvent

Procedure

To a stirred slurry of 126 g of 2-methylamino-5-mercapto-1,3,4-thiadiazole in 525 ml of dioxane containing a few drops of triethylamine is added 49 g of methyl isocyanate. After stirring two hours at room temperature, the solid is collected by filtration and washed with hexane giving 165 g, melting at 162°-3°. This product is heated on the steam bath 11/2 -2 hours with 250 ml of triethylamine, during which time the initial solid is converted to a heavy amber oil. The supernatent liquid is decanted and the oil is dissolved in water and neutralized with dilute hydrochloric acid to pH 2-3. The precipitated solid is collected and washed with water and air dried, giving 132 g of N,N'-dimethyl-N'-(5-mercapto-1,3,4-thiadiazol-2-yl)urea, m.p. 230° (dec.).

Workup

  1. filtrationthe solid is collected by filtration
  2. washwashed with hexane giving 165 g, melting at 162°-3°
  3. temperatureThis product is heated on the steam bath 11/2 -2 hours with 250 ml of triethylamine
  4. customThe supernatent liquid is decanted
  5. dissolutionthe oil is dissolved in water and neutralized with dilute hydrochloric acid to pH 2-3
  6. customThe precipitated solid is collected
  7. washwashed with water and air
  8. customdried

Sources & evidence

ORD record
ord-28f568c20bb949ddb94ba26cb4c1b498
Source dataset
uspto-grants-1977_05
Patent number
US04021225

Reaction notes

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