Diphosgene → 5,5-Dimethyl-3-(3-nitro-4-isopropylphenyl)-1-pyridin-4-ylmethyl-imidazolidine-2,4-dione

HRID 2356940Notes

Reaction equation

HRID 2356940 reaction equation
[O:1]=[C:2](Cl)OC(Cl)(Cl)Cl.[N+:9]([C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][C:18]=1[CH:19]([CH3:21])[CH3:20])[NH2:15])([O-:11])=[O:10].CO[C:24](=[O:36])[C:25]([CH3:35])([NH:27][CH2:28][C:29]1[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=1)[CH3:26]>ClCCCl.C1COCC1>[CH3:35][C:25]1([CH3:26])[N:27]([CH2:28][C:29]2[CH:30]=[CH:31][N:32]=[CH:33][CH:34]=2)[C:2](=[O:1])[N:15]([C:14]2[CH:16]=[CH:17][C:18]([CH:19]([CH3:21])[CH3:20])=[C:12]([N+:9]([O-:11])=[O:10])[CH:13]=2)[C:24]1=[O:36]

Participants

6

Reactant 3

HCID 10426DiphosgeneHCID 221118273-Nitro-4-(propan-2-yl)anilineHCID 43725938HCID 43725938, compound

Product 1

HCID 116609365,5-Dimethyl-3-(3-nitro-4-isopropylphenyl)-1-pyridin-4-ylmethyl-imidazolidine-2,4-dione

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

6.04 g (30 mmol) diphosgene in 50 ml 1,2-dichlorethane were treated at −20° C. with a solution of 2 g (11.1 mmol) 3-nitro-4-isopropyl-aniline in 20 ml 1,2-dichlorethane. The mixture was allowed to come to room temperature and then was heated to 50° C. for 5 h. After standing over night, the solvent was evaporated and the residual oil was taken up in 40 ml THF. 3.93 g (18.7 mmol) 2-methyl-2-[(pyridin-4-ylmethyl)-amino]-propionic acid methyl ester in 30 ml THF were added and the mixture was refluxed for 6 h. The solvent was evaporated and the residue taken up in ethylacetate and washed with water. THe organic phase was dried, the solvent evaporated and the residue was purified by preparative HPLC. (C18 reversed phase column, elution with a water (0.1% trifluoracetic acid)/acetonitrile gradient) Yield: 2.7 g.

Workup

  1. customto come to room temperature
  2. waitAfter standing over night
  3. customthe solvent was evaporated
  4. temperaturethe mixture was refluxed for 6 h
  5. customThe solvent was evaporated
  6. washwashed with water
  7. customTHe organic phase was dried
  8. customthe solvent evaporated
  9. customthe residue was purified by preparative HPLC
  10. washphase column, elution with a water (0.1% trifluoracetic acid)/acetonitrile gradient) Yield: 2.7 g

Sources & evidence

ORD record
ord-58f96f2b67504f08a9f6457e9921f285
Source dataset
uspto-grants-2010_07
Patent number
US07759379B2

Reaction notes

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