Benzyl Alcohol → HCID 67203361, compound

HRID 85104Notes

Reaction equation

HRID 85104 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]([C:9]2[NH:13][C:12]3[CH:14]=[CH:15][CH:16]=[C:17](C(O)=O)[C:11]=3[N:10]=2)[CH:6]=[CH:7][CH:8]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:30])C=CC=CC=1.CC[N:42]([CH2:45]C)CC.[CH2:47]([OH:54])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>C1(C)C=CC=CC=1>[F:21][C:2]([F:22])([F:1])[C:3]1[CH:4]=[C:5]([C:9]2[NH:13][C:12]3[CH:14]=[CH:15][CH:16]=[C:17]([NH:42][C:45](=[O:30])[O:54][CH2:47][C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)[C:11]=3[N:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 672023142-(3-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxylic acid

Product 1

HCID 67203361HCID 67203361, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-(3-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxylic acid (11; 1.53 g, 5.0 mmol), diphenylphosphoryl azide (DPPA, 1.39 g, 5.0 mmol) and Et3N (0.75 g, 7.4 mmol) in toluene (15 mL) was stirred at room temperature for 2 h and then stirred under reflux for 2 h. Benzyl alcohol (0.54 g, 5.0 mmol) was added and the resulting reaction mixture was stirred under reflux for another 12 h. After cooling to room temperature, the mixture was washed successively with aqueous citric acid (10% w/w), saturated NaHCO3 and brine. The organic layer was (Na2SO4), and concentrated under reduced pressure. The resulting residue was purified by chromatography (petroleum ether:ethyl acetate=10:1) to give benzyl 2-(3-(trifluoromethyl)phenyl)-1H-benzo[d]imidazol-4-ylcarbamate 12 (1.45 g, 70%) as a solid. MS (ESI) calcd for C22H16F3N3O2: 411.12; found: 412 [M+H].

Workup

  1. temperatureunder reflux for 2 h
  2. customthe resulting reaction mixture
  3. stirringwas stirred
  4. temperatureunder reflux for another 12 h
  5. washthe mixture was washed successively with aqueous citric acid (10% w/w), saturated NaHCO3 and brine
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by chromatography (petroleum ether:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-a1b20383c4ee4aca8b7d133a45c2a7f2
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Reaction notes

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