Pyridine → (4-Chloro-2-hydroxymethyl-phenyl)-carbamic acid ethyl ester

HRID 1710668Notes

Reaction equation

HRID 1710668 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH2:9][OH:10].Cl[C:12]([O:14][CH2:15][CH3:16])=[O:13].N1C=CC=CC=1>C(Cl)Cl.CCOC(C)=O>[CH2:15]([O:14][C:12](=[O:13])[NH:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH2:9][OH:10])[CH3:16]

Participants

6

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 5867542-Amino-5-chlorobenzyl alcohol

Product 1

HCID 58834345(4-Chloro-2-hydroxymethyl-phenyl)-carbamic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2-amino-5-chloro-phenyl)-methanol (1.58 g, 10 mmol, 1 equiv) in 15 mL of DCM was slowly added ethyl chloroformate (1.05 mL, 1.1 equiv) and pyridine (1.2 mL, 1.5 equiv). After stirring for 1 h, the resultant mixture was diluted with EtOAc and washed with water. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to provide the crude product, (4-Chloro-2-hydroxymethyl-phenyl)-carbamic acid ethyl ester (71), which was used in subsequent reactions without further purification.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6d1b61845b72467198110849ac1dfade
Source dataset
uspto-grants-2010_09
Patent number
US07790726B2

Reaction notes

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