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

HRID 1421380Notes

Reaction equation

HRID 1421380 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-80a3469d9d0e4c9297b92a5b8a2f67bf
Source dataset
uspto-grants-2000_06
Patent number
US06075148

Reaction notes

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