1,1'-Carbonyldiimidazole → HCID 22177242, compound

HRID 1797167Notes

Reaction equation

HRID 1797167 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][CH2:10][CH2:11][NH:12][CH2:13][CH:14]([C:18]2[CH:23]=[CH:22][C:21]([I:24])=[CH:20][CH:19]=2)[CH2:15][CH:16]=[CH2:17])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C1N=CN([C:30](N2C=NC=C2)=[O:31])C=1>C1(C)C=CC=CC=1.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:10][CH2:11][N:12]([CH2:13][CH:14]([C:18]3[CH:19]=[CH:20][C:21]([I:24])=[CH:22][CH:23]=3)[CH2:15][CH:16]=[CH2:17])[C:30]2=[O:31])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 22177252HCID 22177252, compound

Product 1

HCID 22177242HCID 22177242, compoundYield 31.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of N-(3,5-dichloro-phenyl)-N′-[2-(4-iodo-phenyl)-pent-4-enyl]-ethane-1,2-diamine (0.386 g, 0.81 mmol) in toluene (10 mL) was added CDI (0.18 g, 1.1 mmol, 1.4 eq). The mixture was heated to 100° C. for 16 h, then cooled to room temperature, diluted with EtOAc (25 mL) and washed twice with saturated aqueous NaCl (25 mL). The organic extracts were dried over sodium sulfate, filtered and concentrated by rotary evaporation to give a dark brown oil. The crude product was purified by flash column chromatography eluting with 10% EtOAc/hexanes to give 1-(3,5-dichloro-phenyl)-3-[2-(4-iodo-phenyl)-pent-4-enyl]-imidazolidin-2-one (0.128 g, 0.255 mmol, 30%) as a pale foam. 1H NMR (300 MHz, CDCl3): δ 7.74 (d, 2H), 7.54 (d, 2H), 7.20 (m, 3H), 5.75 (m, 1H), 5.10 (m, 2H), 3.74 (m, 3H), 3.38 (m, 2H), 3.22 (m, 1H), 3.08 (m, 1H), 2.50 (m, 2H).

Workup

  1. temperaturecooled to room temperature
  2. washwashed twice with saturated aqueous NaCl (25 mL)
  3. dry with materialThe organic extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation
  6. customto give a dark brown oil
  7. customThe crude product was purified by flash column chromatography
  8. washeluting with 10% EtOAc/hexanes

Sources & evidence

ORD record
ord-542e32656726457ba21af3f182358482
Source dataset
uspto-grants-2006_04
Patent number
US07034056B2

Reaction notes

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