Guaiacol → N-ME-2-METHOXYPHENYLCARBAMATE

HRID 1447087Notes

Reaction equation

HRID 1447087 reaction equation
[SH2]=N.CNC(C1C=CC=CC=1C(O)=O)=[O:6].C([N:18]([CH2:21]C)[CH2:19]C)C.O.[CH3:24][O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[OH:32]>CC(C)=O>[CH3:21][NH:18][C:19](=[O:6])[O:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[O:25][CH3:24]

Participants

6

Reactant 4

HCID 460GuaiacolHCID 962WaterHCID 8471TriethylamineHCID 178485307HCID 178485307, compound

Product 1

HCID 77539N-ME-2-METHOXYPHENYLCARBAMATE

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

5 g of N-methyl-carbamoyl-benzoic acid sulfimide are suspended in a mixture of 2.6 g of 2-methoxyphenol and 50 ml acetone and while stirring at room temperature, a solution of 2.9 ml triethylamine in 30 ml acetone was added dropwise, in an hour. The mixture is stirred for an additional 2 hours at room temperature, then 240 ml of distilled water are slowly added to the mixture and extracted with 3×30 ml of ether. The ethereal extract is dried with sodium sulfate, the solvent is evaporated in a vacuum at a temperature not above 30° C. 2.43 g of 2-methoxy-phenyl N-methyl-carbamate are obtained, recrystallized from N-pentane, melting at 90°-92° C.

Workup

  1. stirringThe mixture is stirred for an additional 2 hours at room temperature
  2. extractionextracted with 3×30 ml of ether
  3. extractionThe ethereal extract
  4. dry with materialis dried with sodium sulfate
  5. customthe solvent is evaporated in a vacuum at a temperature not above 30° C

Sources & evidence

ORD record
ord-1b39aad43658450e949d62ec81ab4748
Source dataset
uspto-grants-1982_02
Patent number
US04315861

Reaction notes

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