Tris(hydroxymethyl)aminomethane → 1-{3-[1-(3,5-dichloro-benzyl)-1H-imidazol-2-ylmethoxy]-phenyl}-3-phenyl-urea

HRID 2101522Notes

Reaction equation

HRID 2101522 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[C:21]([Cl:23])[CH:22]=1)[CH2:5][N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([NH2:19])[CH:16]=[CH:17][CH:18]=1.C(O)C(N)(CO)CO.[C:32]1([N:38]=[C:39]=[O:40])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[C:21]([Cl:23])[CH:22]=1)[CH2:5][N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([NH:19][C:39]([NH:38][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:40])[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 7672Phenyl isocyanateHCID 119510703-[1-(3,5-Dichloro-benzyl)-1H-imidazol-2-ylmethoxy]-phenylamine

Product 1

HCID 119512391-{3-[1-(3,5-dichloro-benzyl)-1H-imidazol-2-ylmethoxy]-phenyl}-3-phenyl-ureaYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-[1-(3,5-Dichloro-benzyl)-1H-imidazol-2-ylmethoxy]-phenylamine (see Example 21) in CH2Cl2 and phenyl isocyanate in CH2Cl2 (0.4 mL) were combined and the reaction was shaken at room temperature. After 72 h, LC/MS showed the reaction had progressed to completion. Trisamine resin was added and the reaction was shaken at room temperature. After 4 h, the reaction was filtered and the resin was washed with CH2Cl2 (2 mL). The filtrates were combined and concentrated in vacuo. Preparatory TLC (silica, 20:1 CH2Cl2:MeOH; Rf=0.5) yielded 1-{3-[1-(3,5-dichloro-benzyl)-1H-imidazol-2-ylmethoxy]-phenyl}-3-phenyl-urea (25a) as a white solid (22 mg, 52%); MS m/z 467 [C24H20Cl2N4O2+H]+.

Workup

  1. stirringthe reaction was shaken at room temperature
  2. waitAfter 4 h
  3. filtrationthe reaction was filtered
  4. washthe resin was washed with CH2Cl2 (2 mL)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-76f95c6259324b2c91259a770c8caf71
Source dataset
uspto-grants-2009_08
Patent number
US07572921B2

Reaction notes

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