Acetyl chloride → HCID 68802695, compound

HRID 1270761Notes

Reaction equation

HRID 1270761 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]([OH:16])[CH:12]=2)[CH:7]=1)[CH3:2].C(N(CC)CC)C.[C:25](Cl)(=[O:27])[CH3:26]>ClCCl>[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]([O:16][C:25](=[O:27])[CH3:26])[CH:12]=2)[CH:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 68802648HCID 68802648, compound

Product 1

HCID 68802695HCID 68802695, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(6-hydroxy-2-naphthyl)carbamic acid ethyl ester (1 g, 4.32 mmol) and triethylamine (1.80 mL, 13 mmol) in dichloromethane (20 mL) at room temperature, is added acetyl chloride (0.369 mL, 5.19 mmol) dropwise. After stirring at room temperature for 3 hours, the reaction mixture is concentrated and purified by flash chromatography on silica gel (2:1 hexane/EtOAc) to give N-(6-acetyloxy-2-naphthyl)carbamic acid ethyl ester as a white solid.

Workup

  1. concentrationthe reaction mixture is concentrated
  2. custompurified by flash chromatography on silica gel (2:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-1d6bb87ed98e480b8fc114ea6e610906
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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