Methyl Isocyanate → HCID 135689600, compound

HRID 434726Notes

Reaction equation

HRID 434726 reaction equation
[OH:1][C:2]1[CH:18]=[C:17]([OH:19])[CH:16]=[CH:15][C:3]=1[CH:4]=[N:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([OH:13])=[CH:8][C:7]=1[CH3:14].[CH3:20][N:21]=[C:22]=[O:23]>C([O-])(=O)C.C([O-])(=O)C.C([Sn+2]CCCC)CCC.C(OCC)(=O)C>[CH3:20][NH:21][C:22](=[O:23])[O:13][C:9]1[CH:10]=[C:11]([CH3:12])[C:6]([N:5]=[CH:4][C:3]2[CH:15]=[CH:16][C:17]([O:19][C:22](=[O:23])[NH:21][CH3:20])=[CH:18][C:2]=2[OH:1])=[C:7]([CH3:14])[CH:8]=1

Participants

5

Reactant 2

HCID 12228Methyl IsocyanateHCID 135689604HCID 135689604, compound

Product 1

HCID 135689600HCID 135689600, compoundYield 97.5%

Reagents, catalysts & solvents 2

HCID 9798523Di-n-butyl diacetoxy tinCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

To a 350 milliliter glass pressure bottle equipped with a magnetic stirrer was added 5.15 grams (0.020 moles) of 4-(2,4-dihydroxybenzylideneamino)-3,5-dimethylphenol prepared in Part A, 2.40 grams (0.042 moles) of methyl isocyanate, 100 milliliters of ethyl acetate and 5 drops of dibutyltin diacetate. The resulting reaction mixture was stirred for 18 hours at room temperature, diluted with an additional 100 milliliters of ethyl acetate and washed twice with a 1% aqueous sodium bicarbonate solution followed by a single wash with saturated brine solution. After drying the reaction mixture over magnesium sulfate, it was concentrated under reduced pressure to give 7.25 grams (0.0195 moles) of 4-[2-hydroxy-4-(methylcarbamoyloxy)benzylideneamino]-3,5-dimethylphenyl methylcarbamate in the form of a yellow solid having a melting point of 70°-65° C. and the following structural formula: ##STR19##

Workup

  1. customThe resulting reaction mixture
  2. washwashed twice with a 1% aqueous sodium bicarbonate solution
  3. washa single wash with saturated brine solution
  4. dry with materialAfter drying the reaction mixture over magnesium sulfate, it
  5. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-e3d72a7d062947179f50b89bb939ce24
Source dataset
uspto-grants-1983_08
Patent number
US04399148

Reaction notes

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