Potassium Carbonate → Carbamic acid, hydroxy(2-methylphenyl)-, phenyl ester

HRID 1602124Notes

Reaction equation

HRID 1602124 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][OH:9].[C:10]([O-:13])([O-])=[O:11].[K+].[K+]>C(Cl)Cl>[OH:9][N:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1])[C:10](=[O:11])[O:13][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 11908N-Hydroxy-2-toluidine

Product 1

HCID 15767249Carbamic acid, hydroxy(2-methylphenyl)-, phenyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2.5 g (20 mmol) of N-(2-methylphenyl)-hydroxylamine (crude product, obtained according to Bamberger et al., Anm. Chem. 316 (1901), 278), 3.5 g (25 mmol) of K2CO3 and 3.5 g (22 mmol) of phenyl Chlorooformate in 20 ml of CH2Cl2 is stirred for 2 hours at room temperature. The reaction mixture is then extracted with water, dried over MgSO4 and evaporated down. The residue is purified by column chromatography with mixtures of cyclohexane and ethyl acetate. There is obtained 2.0 g (8.2 mmol=42%) of the title compound as a colorless solid (mp=98° C.).

Workup

  1. extractionThe reaction mixture is then extracted with water
  2. dry with materialdried over MgSO4
  3. customevaporated down
  4. customThe residue is purified by column chromatography with mixtures of cyclohexane and ethyl acetate

Sources & evidence

ORD record
ord-87434f320b5b4a9989a6ea0bb5b38f10
Source dataset
uspto-grants-1999_11
Patent number
US05981532

Reaction notes

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