Chlorotrimethylsilane → 1-(Triphenylmethyl)-1H-imidazole-4-propanoic acid

HRID 1167445Notes

Reaction equation

HRID 1167445 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][CH2:7][C:8]([OH:10])=[O:9])[N:3]=[CH:2]1.C[Si](Cl)(C)C.C(N(CC)CC)C.Cl[C:24]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>ClCCl.C(#N)C.CO>[C:25]1([C:24]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[N:1]2[CH:5]=[C:4]([CH2:6][CH2:7][C:8]([OH:10])=[O:9])[N:3]=[CH:2]2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

8

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 6456Trityl chlorideHCID 8471Triethylamine2×HCID 178525356HCID 178525356, compound

Product 1

HCID 74084421-(Triphenylmethyl)-1H-imidazole-4-propanoic acidYield 82.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent2×

Procedure

3-(4-Imidazolyl)propionic acid (1.0 g, 7.1 mmol) was suspended in a mixture of dichloromethane (5 ml) and acetonitrile (25 ml). Trimethylsilyl chloride (781 mg, 7.2 nmmol) was added and the mixture refluxed for 4 hours. Triethylamine (1 ml) was added, and refluxing continued for 15 minutes. Cooled, triethylamine (1 ml) added followed by chlorotriphenylmethane (1.99 g, 7.1 mmol) in dichloromethane (10 ml), and the mixture stirred at ambient temperature for 2 hours. MeOH (20 ml) was added, the mixture stirred for 30 minutes, then evaporated to dryness. Water (50 ml) was added to the residue, and the pH adjusted to 8-8.5 with triethylamine. The precipitate was filtered off, washed with diethyl ether, and dried to give the desired product (2.25 g). MS (ESP): 383 (MH+) for C25H22N2O2;

Workup

  1. temperaturethe mixture refluxed for 4 hours
  2. temperaturerefluxing
  3. temperatureCooled
  4. stirringthe mixture stirred for 30 minutes
  5. customevaporated to dryness
  6. additionWater (50 ml) was added to the residue
  7. filtrationThe precipitate was filtered off
  8. washwashed with diethyl ether
  9. customdried

Sources & evidence

ORD record
ord-ad6a48cc776640f1baf8c40bbc12dd69
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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