Nitrogen → HCID 21082125, compound

HRID 346701Notes

Reaction equation

HRID 346701 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])=[NH:10])=[CH:4][CH:3]=1.Cl[C:20](=[CH2:23])[C:21]#[N:22].C(N(CC)C(C)C)(C)C.N#N>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:23][CH:20]([C:21]#[N:22])[N:10]=[C:9]2[C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 947NitrogenHCID 701982-ChloroacrylonitrileHCID 81531DiisopropylethylamineHCID 178512018HCID 178512018, compound

Product 1

HCID 21082125HCID 21082125, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Part A: A magnetically stirred mixture of N-(4-chlorophenyl)-2,4-dichlorobenzenecarboxamidine (10.0 gram, 0.033 mol), 2-chloroacrylonitrile (5.7 gram, 0.065 mol) and N,N-diisopropylethylamine (DIPEA) (12.5 ml, 0.069 mol) in tetrahydrofuran (150 ml) is heated at reflux temperature for 40 hours (N2 atmosphere). After cooling to room temperature the mixture is concentrated in vacuo. The residue is dissolved in a mixture of dichloromethane and water (200 ml/200 ml). The dichloromethane layer is collected, dried over MgSO4, filtered and concentrated in vacuo. The residue is recrystallised from ethanol/water to give 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-4,5-dihydro-1H-imidazole-4-carbonitrile (11.23 gram, 97% yield). 1H-NMR (400 MHz, CDCl3): δ 4.28 (dd, J=10 and 8 Hz, 1H), 4.36 (t, J=10 Hz, 1H), 5.07 (dd, J=10 and 8 Hz, 1H), 6.68 (br d, J=8 Hz, 2H), 7.16 (br d, J=8 Hz, 2H), 7.32–7.36 (m, 2H), 7.45 (d, J=8 Hz, 1H).

Workup

  1. temperatureis heated
  2. concentrationis concentrated in vacuo
  3. dissolutionThe residue is dissolved in a mixture of dichloromethane and water (200 ml/200 ml)
  4. customThe dichloromethane layer is collected
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is recrystallised from ethanol/water

Sources & evidence

ORD record
ord-5cc7d5a01a2841c094620c98cc21b1a9
Source dataset
uspto-grants-2007_02
Patent number
US07173044B2

Reaction notes

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