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

HRID 1005469Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][OH:9].C([O-])(O)=O.[Na+].Cl[C:16]([O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:17].O>C(Cl)Cl>[OH:9][N:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1])[C:16](=[O:17])[O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: -10 °C

Procedure

A mixture of 350 g (purity about 80%; 2.3 mol; prepared by a similar method to Bamberger et al., Ann. Chem. 316 (1901), 278) of N-(2-methylphenyl)hydroxylamine and 286.8 g (3.4 mol) of NaHCO3 in 700 ml of CH2Cl2 is treated with 447 g (2.85 mol) of phenyl chloroformate with vigorous stirring at about -10° C. The mixture is stirred for about 1 hour at -10° C. and 600 ml of water are then added dropwise, the temperature of the reaction mixture increasing to 5-10° C. and a vigorous evolution of gas occurring. The aqueous phase is then separated off and extracted once more with CH2Cl2. The combined organic phases are extracted with water, dried over MgSO4 and concentrated. The residue crystallizes and is stirred with cyclohexane. 407 g (72%) of the title compound are obtained as a colorless solid.

Workup

additionA mixture of 350 g (purity about 80%
customprepared by a similar method to Bamberger et al., Ann
stirringThe mixture is stirred for about 1 hour at -10° C.
temperaturethe temperature of the reaction mixture increasing to 5-10° C.
customThe aqueous phase is then separated off
extractionextracted once more with CH2Cl2
extractionThe combined organic phases are extracted with water
dry with materialdried over MgSO4
concentrationconcentrated
customThe residue crystallizes
stirringis stirred with cyclohexane

Sources & evidence

ORD record: ord-1e8fd1c2c8284c5e8e1aa49b73deac4e
Source dataset: uspto-grants-2000_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06054592

Reaction notes

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