Methyl Isocyanate → HCID 13241794, compound

HRID 1632241Notes

Reaction equation

HRID 1632241 reaction equation
C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC.[CH3:38][N:39]=[C:40]=[O:41].[I:42][C:43]#[C:44][CH2:45][O:46][CH2:47][CH2:48][OH:49]>C(Cl)CCl>[CH3:38][NH:39][C:40](=[O:41])[O:49][CH2:48][CH2:47][O:46][CH2:45][C:44]#[C:43][I:42]

Participants

5

Reactant 3

HCID 12228Methyl IsocyanateHCID 926232-((3-Iodopropin-2-yl)oxy)ethanolHCID 9809426Di-n-butyldilauryltin

Product 1

HCID 13241794HCID 13241794, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

One milliliter of dibutyltin dilaurate was added under agitation as catalyst to a solution of 3.3 gm (0.058 mol) of methyl isocyanate and 12.8 gm (0.057 mol) of 2-(3-iodo-2-propynyloxy)-ethanol in 50 ml ethylene chloride. Due to the exothermic reaction, the temperature rose gradually from room temperature to 30° C. After a reaction time of 16 hours, the solvent was removed by distillation under vacuum, and the yellowish oil obtained was extracted with n-hexane to separate the catalyst, the hexane phase being discarded. Then, the residual solvent was removed under vacuum,, and 15.6 gm of 2-(3-iodo-2-propynyloxy)-ethyl N-methyl-carbamate (97% of theory) were obtained as a clear, yellowish oil, which crystallized into a colorless solid (melting point: 52°-55° C). Solubility: dissolves readily in ethanol or acetone; almost insoluble in water.

Workup

  1. customDue to the exothermic reaction
  2. customrose gradually from room temperature to 30° C
  3. customAfter a reaction time of 16 hours, the solvent was removed by distillation under vacuum
  4. customthe yellowish oil obtained
  5. extractionwas extracted with n-hexane
  6. customto separate the catalyst
  7. customThen, the residual solvent was removed under vacuum

Sources & evidence

ORD record
ord-76dac80dcbb649888d5ed31daf77f038
Source dataset
uspto-grants-1984_10
Patent number
US04474807

Reaction notes

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