Triethylamine → tert-butyl2-methyl-1H-benzo[d]imidazole-1-carboxylate

HRID 1601094Notes

Reaction equation

HRID 1601094 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.CCN(CC)CC.[O:18](C(OC(C)(C)C)=O)[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=O>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:19]([N:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[CH3:1])([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:18]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 119842-MethylbenzimidazoleHCID 90495Di-tert-butyl dicarbonate

Product 1

HCID 11183867tert-butyl2-methyl-1H-benzo[d]imidazole-1-carboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-methylbenzimidazole (1.5 g, 11.35 mmole), Et3N (1.66 mL, 11.92 mmole), DMAP (0.20 g, 1.6 mmole), and (BOC)2O (2.60 g, 11.92 mmole) in anhydrous CH2Cl2 (15 mL) was stirred at RT for 24 hr, then was concentrated. The residue was taken up in H2O, stirred, and filtered to afford the title compound (2.63 g, 100%) as a colorless solid: mp 71-72° C.

Workup

  1. concentrationwas concentrated
  2. stirringstirred
  3. filtrationfiltered

Sources & evidence

ORD record
ord-60034c79c38d422194d7452195f25780
Source dataset
uspto-grants-1999_11
Patent number
US05977101

Reaction notes

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