Triethylamine → Benzimidazole

HRID 222905Notes

Reaction equation

HRID 222905 reaction equation
ClC1C(Cl)=C(OC(C)C)C=CC=1C(N[C@@H](C[C:12]1[CH:17]=[CH:16][C:15]([C:18]2[N:19]=[C:20]3C(C)=CC=C[N:21]3[CH:27]=2)=CC=1)CCO)=O.C(N(CC)CC)C.FC(F)(F)C(OC1C(F)=C(F)C(F)=C(F)C=1F)=O>>[N:21]1[C:27]2[CH:12]=[CH:17][CH:16]=[CH:15][C:18]=2[NH:19][CH:20]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 4327891Pentafluorophenyl TrifluoroacetateHCID 57594459HCID 57594459, compound

Product 1

HCID 5798BenzimidazoleYield 193.1%

Procedure

To a 0° C. crude solution of compound 2 (4.1 g, 15.34 mmol) and triethylamine (6.4 mL, 46.02 mmol) in dicholoromethane (200 mL) was added pentafluorophenyl trifluoroacetate (6.35 mL, 36.82 mmol) via syringe over 3 min. After another 5 min, the ice bath was removed and the reaction mixture stirred while warming to room temperature for another 2 hours. The reaction mixture was concentrated in vacuo, and the resulting residue purified by flash chromatography (silica gel, hexanes/ethyl acetate=1:0, 50:1) to give compound 3 (3.5 g, 50% yield).

Workup

  1. customthe ice bath was removed
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe resulting residue purified by flash chromatography (silica gel, hexanes/ethyl acetate=1:0, 50:1)

Sources & evidence

ORD record
ord-c582dde2de1b4aa6acc47027a4ba6058
Source dataset
uspto-grants-2012_06
Patent number
US08207340B2

Reaction notes

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