Hydrochloric Acid → Phenyl N-(2-chloro-4-hydroxyphenyl)carbamate

HRID 869488Notes

Reaction equation

HRID 869488 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[Cl:9].N1C=CC=CC=1.Cl[C:17]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:18].Cl>CN(C)C=O.C(OCC)(=O)C.O>[Cl:9][C:3]1[CH:4]=[C:5]([OH:8])[CH:6]=[CH:7][C:2]=1[NH:1][C:17](=[O:18])[O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 15891Phenyl chloroformateHCID 871844-Amino-3-chlorophenol

Product 1

HCID 11277058Phenyl N-(2-chloro-4-hydroxyphenyl)carbamate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 4-amino-3-chlorophenol (23.7 g) in N,N-dimethylformamide (100 mL) was added pyridine (23.4 mL) while cooling in an ice bath, and phenyl chloroformate (23.2 mL) was added dropwise below 20° C. After stirring at room temperature for 30 min, water (400 mL), ethyl acetate (300 mL), and 6N—HCl (48 mL) were added and stirred. The organic layer was separated, washed twice with a 10% aqueous sodium chloride solution (200 mL), and dried over magnesium sulfate. The solvent was evaporated to give 46 g of the titled compound as a solid.

Workup

  1. temperaturewhile cooling in an ice bath
  2. stirringstirred
  3. customThe organic layer was separated
  4. washwashed twice with a 10% aqueous sodium chloride solution (200 mL)
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-ed2df2442ec44fdeb272a87a6d5aae69
Source dataset
uspto-grants-2015_03
Patent number
US08969379B2

Reaction notes

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