Methyl Isocyanate → HCID 13937121, compound

HRID 651907Notes

Reaction equation

HRID 651907 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([OH:8])[CH:5]=[C:4]([C:9]([Cl:12])([Cl:11])[Cl:10])[CH:3]=1.[CH3:13][N:14]=[C:15]=[O:16]>CN(C)C=O.C(N(CC)CC)C>[CH3:13][NH:14][C:15](=[O:16])[O:8][C:6]1[CH:5]=[C:4]([C:9]([Cl:12])([Cl:10])[Cl:11])[CH:3]=[C:2]([Cl:1])[N:7]=1

Participants

5

Reactant 2

HCID 12228Methyl IsocyanateHCID 178516063HCID 178516063, compound

Product 1

HCID 13937121HCID 13937121, compound

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution was prepared by dissolving 7.4 g (0.03 m) of 6-chloro-4-(trichloromethyl)-2-pyridinol in 45 ml of dry dimethylformamide. To this solution was added 1.71 g (0.03 m) of methyl isocyanate and 7 drops of triethylamine. The mixture was allowed to stand, at room temperature, for ~30 hours. The reaction mixture was then poured over ice and the resulting solids were filtered out and taken up in hexane. The above-named product was recrystallized from the hexane and recovered in a yield of 3.8 g. The product melted at 95.5°-99.5° C. The structure of the compound was confirmed by its IR spectrum. Upon analysis, the product was found to have carbon, hydrogen, nitrogen and chlorine contents of 31.90, 2.10, 9.10 and 46.26 percent, respectively, as compared with the theoretical contents of 31.50, 1.99, 9.22 and 46.50 percent, respectively, as calculated for the above-named compound (Compound 2).

Workup

  1. customA solution was prepared
  2. waitto stand, at room temperature, for ~30 hours
  3. additionThe reaction mixture was then poured over ice
  4. filtrationthe resulting solids were filtered out
  5. customThe above-named product was recrystallized from the hexane
  6. customrecovered in a yield of 3.8 g

Sources & evidence

ORD record
ord-22d2fec1123348f587645ce118ba7889
Source dataset
uspto-grants-1987_06
Patent number
US04670045

Reaction notes

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