Trimethylsilyl isocyanate → HCID 178514076, compound

HRID 1930736Notes

Reaction equation

HRID 1930736 reaction equation
[O:1]([CH2:8][C:9]1[NH:10][CH:11]=[C:12]([C:14]2[CH:27]=[CH:26][C:17]([O:18][C:19]3[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=3)=[CH:16][CH:15]=2)[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N:32]=[C:33]=[O:34])(C)C>O1CCCC1>[O:1]([CH2:8][C:9]1[NH:10][CH:11]=[C:12]([C:14]2[CH:27]=[CH:26][C:17]([O:18][C:19]3[CH:20]=[CH:21][C:22]([NH:23][C:33]([NH2:32])=[O:34])=[CH:24][CH:25]=3)=[CH:16][CH:15]=2)[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70696Trimethylsilyl isocyanateHCID 178507748HCID 178507748, compound

Product 1

HCID 178514076HCID 178514076, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture containing 4-{4-[2-(phenoxymethyl)-1H-imidazol-4-yl]phenoxy}aniline (0.2 g, 0.56 mmol) and trimethylsilyl-isocyanate (0.11 ml, 0.84 mmol) in 3 ml of tetrahydrofuran is stirred for 24 hours at ambient temperature. Aminomethylpolystyrene resin EHL (Novabiochem, 200-400 mesh, 2% DVB) (200 mg, approximately 1 mmol) is added and stirring is maintained for three hours. After filtration on frit, the filtrate is concentrated in a rotavapor. Isopropyl acetate and traces of isopropanol are added to the residue obtained. The mixture is heated to dissolution followed by filtration on frit then left to crystallize for 24 hours. After filtration then drying under a bell jar, a light beige-coloured powder is obtained.

Workup

  1. additionAminomethylpolystyrene resin EHL (Novabiochem, 200-400 mesh, 2% DVB) (200 mg, approximately 1 mmol) is added
  2. stirringstirring
  3. temperatureis maintained for three hours
  4. filtrationAfter filtration on frit
  5. concentrationthe filtrate is concentrated in a rotavapor
  6. additionIsopropyl acetate and traces of isopropanol are added to the residue
  7. customobtained
  8. temperatureThe mixture is heated to dissolution
  9. filtrationfollowed by filtration on frit
  10. waitthen left
  11. customto crystallize for 24 hours
  12. filtrationAfter filtration
  13. customthen drying under a bell jar
  14. customa light beige-coloured powder is obtained

Sources & evidence

ORD record
ord-4fcf0e8438ab4d0c9270ea418e97d404
Source dataset
uspto-grants-2012_05
Patent number
US08188133B2

Reaction notes

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