Hydrochloric Acid → N-(1,6-dichloro-2-naphthyl)carbamic acid ethyl ester

HRID 1270772Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:17])[NH:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Cl:16])[CH:12]=2)[CH:7]=1)[CH3:2].[Cl:18]N1C(=O)CCC1=O.Cl.O>C(O)(=O)C>[CH2:1]([O:3][C:4](=[O:17])[NH:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Cl:16])[CH:12]=2)[C:7]=1[Cl:18])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of N-(6-chloro-2-naphthyl)carbamic acid ethyl ester (725 mg, 2.90 mmol), N-chlorosuccinimide (387 mg, 2.90 mmol) and 1 M HCl in acetic acid (2.90 mL, 2.90 mmol) in acetic acid (20 mL) is heated at 50° C. under N2 atmosphere for 1 hour. After cooling to room temperature, water (10 mL) is added and extracted with EtOAc. The organic layer is washed with brine, dried (Na2SO4) and concentrated by rotary evaporator to give N-(1,6-dichloro-2-naphthyl)carbamic acid ethyl ester as a yellow solid.

Workup

temperatureAfter cooling to room temperature
extractionextracted with EtOAc
washThe organic layer is washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated by rotary evaporator

Sources & evidence

ORD record: ord-172da2645f774c2ab22370424b1158b9
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07202364B2

Reaction notes

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