Methyl Isocyanate → HCID 54080152, compound

HRID 1380952Notes

Reaction equation

HRID 1380952 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH:9]=[N:10][O:11][CH2:12][C:13]#[CH:14])[CH:3]=1.[CH3:15][N:16]=[C:17]=[O:18]>C(N(CC)CC)C.C(Cl)Cl.O>[CH3:15][NH:16][C:17](=[O:18])[O:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[CH:9]=[N:10][O:11][CH2:12][C:13]#[CH:14]

Participants

6

Reactant 2

HCID 12228Methyl IsocyanateHCID 136045523HCID 136045523, compound

Product 1

HCID 54080152HCID 54080152, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 8471TriethylamineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2.4 grams (0.011 mole) of 4-chloro-2-[(2-propynoxyimino)methyl]phenol (Example 1 product), 0.7 gram (0.013 mole) of methyl isocyanate and three drops of triethylamine in 50 ml of methylene chloride was stirred at ambient temperature for 16 hours. The reaction mixture was concentrated under reduced pressure to give a residual solid. The residue was recrystallized from toluene-hexane to give a solid; mp 97°-100° . The solid was slurried in hot water and collected by filtration. A second recrystallization from toluene-hexane gave 2.2 grams of 4-chloro-2-[(2-propynoxyimino)methyl]phenyl methylcarbamate; mp 99.5°-100.5°.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto give a residual solid
  3. customThe residue was recrystallized from toluene-hexane
  4. customto give a solid
  5. filtrationcollected by filtration
  6. customA second recrystallization from toluene-hexane

Sources & evidence

ORD record
ord-6b7e4187c0c34f7fbdf88e7d9633b185
Source dataset
uspto-grants-1986_04
Patent number
US04584318

Reaction notes

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