Benzene → HCID 21429232, compound

HRID 437593Notes

Reaction equation

HRID 437593 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:8][N:9]=[C:10]=[O:11].[CH:12]1[CH:17]=[CH:16][CH:15]=[CH:14]C=1>C([O-])(=O)C.C([O-])(=O)C.C([Sn+2]CCCC)CCC>[C:1]1([O:7][C:10](=[O:11])[NH:9][CH3:8])[C:6]2[CH:16]3[CH2:15][CH:14]([CH:12]=[CH:17]3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 996Phenol2×HCID 12228Methyl Isocyanate

Product 1

HCID 21429232HCID 21429232, compound

Reagents, catalysts & solvents 1

HCID 9798523Di-n-butyl diacetoxy tinCatalyst

Conditions

Temperature
100 °C

Procedure

##STR7## The phenol, II (1.2 g.) was dissolved in benzene (50 ml.) and placed in a pressure bottle. Methyl isocyanate (0.43 g.) was added followed by two drops of dibutyltin diacetate. The solution was then heated at 100° C. overnight. Removal of the solvent gave a light yellow solid (1.5 g.), which recrystallized from methyl ethyl ketone to give the carbamate V, (0.9 g.) m.p., 158°-162° C. The structure was confirmed by the infrared spectrum, (C=O at 5.8μ as expected from the product).

Workup

  1. customRemoval of the solvent
  2. customgave a light yellow solid (1.5 g.), which
  3. customrecrystallized from methyl ethyl ketone

Sources & evidence

ORD record
ord-bd9bb7fa96334f1894d71c847d89caec
Source dataset
uspto-grants-1977_06
Patent number
US04031237

Reaction notes

Loading…