Hydrochloric Acid → ME-92

HRID 1986976Notes

Reaction equation

HRID 1986976 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:18])OC1C=CC=CC=1.O.[C:20](OCC)(=O)[CH3:21].Cl.C[N:28]([CH3:31])C=O>C1(N)CC1>[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]([NH:28][CH:31]1[CH2:21][CH2:20]1)=[O:18]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 11277058Phenyl N-(2-chloro-4-hydroxyphenyl)carbamate

Product 1

HCID 23135084ME-92Yield 77%

Reagents, catalysts & solvents 1

HCID 69828CyclopropylamineSolvent

Procedure

After dissolving phenyl N-(2-chloro-4-hydroxyphenyl)carbamate in N,N-dimethylformamide (100 mL), cyclopropylamine (22.7 mL) was added while cooling on ice, and the mixture was stirring at room temperature overnight. Water (400 mL), ethyl acetate (300 mL) and 6N-HCl (55 mL) were then 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. Prism crystals obtained by concentrating the solvent were filtered and washed with heptane to give 22.8 g of the titled compound (77% yield from 4-amino-3-chlorophenol).

Workup

  1. additionwas added
  2. temperaturewhile cooling on ice
  3. stirringthe mixture was stirred
  4. customthe organic layer was separated
  5. washThe organic layer was washed twice with a 10% aqueous solution of sodium chloride (200 mL)
  6. dry with materialdried over magnesium sulfate
  7. customPrism crystals obtained
  8. concentrationby concentrating the solvent
  9. filtrationwere filtered
  10. washwashed with heptane

Sources & evidence

ORD record
ord-513f6367b6d04ec2b01bdacfa68d4f21
Source dataset
uspto-grants-2009_06
Patent number
US07550483B2

Reaction notes

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