Hydrochloric Acid → ME-92

HRID 557485Notes

Reaction equation

HRID 557485 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 stirred overnight at room temperature. 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 10% brine (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 title 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 10% brine (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-400e308257f046759d7da59bd36aa46c
Source dataset
uspto-grants-2011_11
Patent number
US08058474B2

Reaction notes

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