Hydrochloric Acid → ME-92

HRID 869489Notes

Reaction equation

HRID 869489 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.[CH:19]1([NH2:22])[CH2:21][CH2:20]1.O.Cl>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]([NH:22][CH:19]1[CH2:21][CH2:20]1)=[O:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 69828CyclopropylamineHCID 11277058Phenyl N-(2-chloro-4-hydroxyphenyl)carbamate

Product 1

HCID 23135084ME-92Yield 77%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of phenyl N-(2-chloro-4-hydroxyphenyl)carbamate in N,N-dimethylformamide (100 mL) was added cyclopropylamine (22.7 mL) while cooling in an ice bath, and the stirring was continued at room temperature overnight. Water (400 mL), ethyl acetate (300 mL), and 6N—HCl (55 mL) were added thereto, and the mixture was stirred. The organic layer was then separated, washed twice with a 10% aqueous sodium chloride solution (200 mL), and dried over magnesium sulfate. The solvent was evaporated to give prism crystals, which were collected by filtration and washed with heptane to give 22.8 g of the titled compound (yield from 4-amino-3-chlorophenol: 77%).

Workup

  1. temperaturewhile cooling in an ice bath
  2. customThe organic layer was then separated
  3. washwashed twice with a 10% aqueous sodium chloride solution (200 mL)
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated
  6. customto give prism crystals, which
  7. filtrationwere collected by filtration
  8. washwashed with heptane

Sources & evidence

ORD record
ord-b3be12d52daf4451a488438eb32a3ee0
Source dataset
uspto-grants-2015_03
Patent number
US08969379B2

Reaction notes

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