Methyl Isocyanate → Monoisouron

HRID 1155478Notes

Reaction equation

HRID 1155478 reaction equation
[CH3:1][C:2]([C:5]1[O:9][N:8]=[C:7]([NH2:10])[CH:6]=1)([CH3:4])[CH3:3].[CH3:11][N:12]=[C:13]=[O:14]>CN(C)C1C=CN=CC=1.C1C=CC=CC=1>[CH3:1][C:2]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:13]([NH:12][CH3:11])=[O:14])[CH:6]=1)([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 12228Methyl IsocyanateHCID 1714733-Isoxazolamine, 5-(1,1-dimethylethyl)-

Product 1

HCID 186687MonoisouronYield 72.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 241BenzeneSolvent2×

Procedure

A 50 milliliter flask with a magnetic stirring bar, addition funnel, thermometer and condenser/drying tube was charged with 3.0 grams (0.021 mole) of 5-(1,1-dimethylethyl)-3-isoxazolamine, a few crystals of 4-dimethylaminopyridine and 20 milliliters of benzene. The funnel was charged with 2.3 grams (0.040 mole) of methyl isocyanate in 5 milliliters of benzene, which was added dropwise over five (5) minutes. After standing overnight, the mass of crystals which formed was isolated by filtration, washed with hexane, and air dried to give 3.0 grams of white powder of 1-[5-(1,1-dimethylethyl)-3-isoxazolyl]-3-methylurea, M.P. 188°-189° C.

Workup

  1. additionA 50 milliliter flask with a magnetic stirring bar, addition funnel
  2. customthermometer and condenser/drying tube
  3. customthe mass of crystals which formed
  4. customwas isolated by filtration
  5. washwashed with hexane, and air
  6. customdried

Sources & evidence

ORD record
ord-ab3df0f911a54ac28b1b4b932fc9a9bf
Source dataset
uspto-grants-1981_11
Patent number
US04302239

Reaction notes

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