Methyl Isocyanate → HCID 135689618, compound

HRID 434719

Reaction equation

HRID 434719 reaction equation
[OH:1][C:2]1[CH:18]=[CH:17][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].[CH3:19][N:20]=[C:21]=[O:22]>C([O-])(=O)C.C([O-])(=O)C.C([Sn+2]CCCC)CCC.C(OCC)(=O)C>[CH3:19][NH:20][C:21](=[O:22])[O:13][C:9]1[CH:8]=[C:7]([CH3:14])[C:6]([N:5]=[CH:4][C:3]2[CH:15]=[CH:16][CH:17]=[CH:18][C:2]=2[OH:1])=[C:11]([CH3:12])[CH:10]=1

Participants

5

Reactant 2

HCID 12228Methyl IsocyanateHCID 1356896104-(2-Hydroxybenzylideneamino)-3,5-dimethylphenol

Product 1

HCID 135689618HCID 135689618, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 9798523Di-n-butyl diacetoxy tinCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a 350 milliliter glass pressure bottle equipped with a magnetic stirrer was added 6.03 grams (0.025 moles) of 4-(2-hydroxybenzylideneamino)-3,5-dimethylphenol prepared in Part A, 1.71 grams (0.030 moles) of methyl isocyanate, 50 milliliters of ethyl acetate and 5 drops of dibutyltin diacetate. The resulting reaction mixture was stirred for 65 hours at room temperature and then 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 collected by filtration and concentrated under reduced pressure to give a brown oil. The oil was triturated with hexane to give 5.21 grams (0.017 moles) of 4-(2-hydroxybenzylideneamino)-3,5-dimethylphenyl methylcarbamate in the form of a yellow solid having a melting point of 116°-118° C. and the following structural formula: ##STR8##

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. filtrationwas collected by filtration
  6. concentrationconcentrated under reduced pressure
  7. customto give a brown oil
  8. customThe oil was triturated with hexane

Sources & evidence

ORD record
ord-73312b832c92420cb03e76f4873bfcc8
Source dataset
uspto-grants-1983_08
Patent number
US04399148

Linked notes

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