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

HRID 1986975Notes

Reaction equation

HRID 1986975 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

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

Workup

  1. additionwas added dropwise below 20° C
  2. stirringthe mixture was stirred
  3. customthe organic layer was separated
  4. washThe organic layer was washed twice with a 10% aqueous solution of sodium chloride (200 mL)
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-bf8f2c66f98146cdb24b23db3a96f4ce
Source dataset
uspto-grants-2009_06
Patent number
US07550483B2

Reaction notes

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