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Potassio isocyanate → Methyl[4-(4-chlorophenyl)-2-oxo-2,3-dihydro-1H-imidazol-1-yl]-acetate

HRID 660904
Notes
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Reaction equation

HRID 660904 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][NH:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:4][CH:3]=1.[N-:17]=[C:18]=[O:19].[K+]>CO.O.O.CO>[CH3:15][O:14][C:12](=[O:13])[CH2:11][N:10]1[CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[NH:17][C:18]1=[O:19]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 11051572Potassio isocyanateHCID 57455761Methyl {[2-(4-chlorophenyl)-2-oxoethyl]amino}acetate

Product 1

HCID 58012289Methyl[4-(4-chlorophenyl)-2-oxo-2,3-dihydro-1H-imidazol-1-yl]-acetate

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent
HCID 22242641
Methanol--water (1/1)
Solvent
2×

Procedure

A solution of 3.41 g (12.27 mmol) of the compound from Example 231A in 14 ml methanol/water (7:3) is added dropwise to a solution of 995 mg (12.27 mmol) of potassium isocyanate in 11 ml methanol/water (7:3). This is stirred for 1 hr at RT. The thick suspension is diluted with 7.4 ml water and 39 ml methanol to facilitate stirring, then heated under reflux for 1 hr and then left to stand overnight at RT. After cooling to 0° C., the precipitate is filtered off, washed with ice-cold water and dried overnight in the drying cabinet at 60° C. 2.84 g (76% of theory) of the title compound are obtained.

Workup

  1. stirringto facilitate stirring
  2. temperatureheated
  3. temperatureunder reflux for 1 hr
  4. waitleft
  5. waitto stand overnight at RT
  6. temperatureAfter cooling to 0° C.
  7. filtrationthe precipitate is filtered off
  8. washwashed with ice-cold water
  9. customdried overnight in the drying cabinet at 60° C

Sources & evidence

ORD record
ord-4b3d73893cdf4447a4b0ee0c5d666f2e
Source dataset
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08084481B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes