Hydrochloric Acid → HCID 68804327, compound

HRID 1270762Notes

Reaction equation

HRID 1270762 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[NH:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16][C:17](=[O:19])[CH3:18])[CH:12]=2)[CH:7]=1)[CH3:2].[Cl:21]N1C(=O)CCC1=O.Cl>C(O)(=O)C>[CH2:1]([O:3][C:4](=[O:20])[NH:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16][C:17](=[O:19])[CH3:18])[CH:12]=2)[C:7]=1[Cl:21])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31398ChlorosuccinimideHCID 68802695HCID 68802695, compound

Product 1

HCID 68804327HCID 68804327, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
50 °C

Procedure

A mixture of N-(6-acetyloxy-2-naphthyl)carbamic acid ethyl ester (670 mg, 2.45 mmol), N-chlorosuccinimide (326 mg, 2.45 mmol) and 1 M HCl in acetic acid (2.45 mL, 2.45 mmol) in acetic acid (10 mL) is heated at 50° C. under N2 atmosphere for 1 hour. After cooling to room temperature the mixture is partitioned between EtOAc and water. The organic layer is washed with brine, dried (Na2SO4) and concentrated by rotary evaporator to give N-(6-acetyloxy-1-chloro-2-naphthyl)carbamic acid ethyl ester as a white solid.

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. customis partitioned between EtOAc and water
  3. washThe organic layer is washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated by rotary evaporator

Sources & evidence

ORD record
ord-0e252996a3284a15bbce91d94206503a
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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