Triethylamine → Benzene, 1-(1-isocyanato-1-methylethyl)-3-methoxy-

HRID 81346Notes

Reaction equation

HRID 81346 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]([CH3:14])([CH3:13])C(O)=O)[CH:6]=[CH:7][CH:8]=1.C([N:17]([CH2:20]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])C=CC=CC=1>C1(C)C=CC=CC=1.CCOC(C)=O>[N:17]([C:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)([CH3:13])[CH3:14])=[C:20]=[O:29]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 108216342-(3-Methoxyphenyl)-2-methylpropanoic acid

Product 1

HCID 10559617Benzene, 1-(1-isocyanato-1-methylethyl)-3-methoxy-

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

2-(3-methoxy-phenyl)-2-methyl-propionic acid (24.40 g) is dissolved in toluene (120 mL) and cooled to 0° C. Triethylamine (16.61 mL) and diphenylphosphorylazide (24.37 g) are added. After 0.5 h the mixture is heated to 110° C. After 3 h the reaction mixture is diluted with EtOAc, cooled to 0° C., extracted with NaHCO3 solution and NaCl solution (H2O, 10%), dried on magnesium sulphate, filtered off from the desiccant and the solvent is eliminated in vacuo. The residue is used in the next reaction step without any further purification.

Workup

  1. temperatureAfter 0.5 h the mixture is heated to 110° C
  2. temperaturecooled to 0° C.
  3. extractionextracted with NaHCO3 solution and NaCl solution (H2O, 10%)
  4. customdried on magnesium sulphate
  5. filtrationfiltered off from the desiccant and the solvent
  6. customThe residue is used in the next reaction step without any further purification

Sources & evidence

ORD record
ord-9c4ef0b6c5a8420a99dfa543c265b92d
Source dataset
uspto-grants-2014_09
Patent number
US08846689B2

Reaction notes

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