Hydrochloric Acid → 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-2(3H)-one

HRID 2189175Notes

Reaction equation

HRID 2189175 reaction equation
[CH3:1][C:2]1([CH3:17])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[C:11]([NH2:16])[C:12]([NH2:15])=[CH:13][CH:14]=2)[O:3]1.[C:18](N1C=CN=C1)(N1C=CN=C1)=[O:19].Cl>C1COCC1>[CH3:8][C:6]1([CH3:7])[C:2]([CH3:17])([CH3:1])[O:3][B:4]([C:9]2[CH:14]=[CH:13][C:12]3[NH:15][C:18](=[O:19])[NH:16][C:11]=3[CH:10]=2)[O:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 177502424-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,2-diamine

Product 1

HCID 438110655-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-2(3H)-oneYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,2-diamine (1.20 g, 5.1 mmol) in anhydrous THF (20 mL) was added 1,1′-carbonyldiimidazole (910 mg, 5.6 mmol). The reaction mixture was stirred at room temperature for 2 hours. The resulting solution was acidified with 1 N HCl (10 mL) and extracted twice with 50 mL portions of Et2O. The combined organic layers were washed with saturated brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give 1.0 g (79%) of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-2(3H)-one. 1H NMR (400 MHz, CDCl3): δ 7.46 (dd, 1H), 7.40 (s, 1H), 7.35 (dd, 1H), 1.35 (s, 12H). MS (EI) for C13H17BN2O3: 261 (MH+).

Workup

  1. extractionextracted twice with 50 mL portions of Et2O
  2. washThe combined organic layers were washed with saturated brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-46e4d5fa63cb4e21bf0bf3b310f26f61
Source dataset
uspto-grants-2012_12
Patent number
US08324231B2

Reaction notes

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