Ethanol → 5-azido-1,2,7-trimethyl-1H-benzimidazole

HRID 1846438Notes

Reaction equation

HRID 1846438 reaction equation
Br[C:2]1[CH:12]=[C:11]([CH3:13])[C:5]2[N:6]([CH3:10])[C:7]([CH3:9])=[N:8][C:4]=2[CH:3]=1.[N-:14]=[N+:15]=[N-:16].[Na+].[Na].O=C1O[C@H]([C@H](CO)O)C(O)=C1O.C(O)C>[Cu]I.O>[N:14]([C:2]1[CH:12]=[C:11]([CH3:13])[C:5]2[N:6]([CH3:10])[C:7]([CH3:9])=[N:8][C:4]=2[CH:3]=1)=[N+:15]=[N-:16]

Participants

7

Reactant 4

HCID 702EthanolHCID 33557Sodium AzideHCID 66586226sodium L-ascorbic acidHCID 669781805-bromo-1,2,7-trimethyl-1H-benzimidazole

Product 1

HCID 866638995-azido-1,2,7-trimethyl-1H-benzimidazole

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

0.59 g (2.50 mmol) 5-bromo-1,2,7-trimethyl-1H-benzimidazole, 0.32 g (4.9 mmol) sodium azide, 75 mg (0.50 mmol) trans-(1R,2R)—N,N′-bismethyl-1,2-cyclohexane-diamine, 50 mg (0.30 mmol) copper(I) iodide and 50 mg (0.30 mmol) L-ascorbic acid sodium salt were added to 2.0 ml of a mixture of ethanol and water (EtOH/water=7/3) and the mixture was stirred for 1 h at 100° C. Then the EtOH was distilled off and the residue was mixed with water. The precipitate formed was suction filtered, washed with water and diethyl ether and dried.

Workup

  1. distillationThen the EtOH was distilled off
  2. additionthe residue was mixed with water
  3. customThe precipitate formed
  4. filtrationfiltered
  5. washwashed with water and diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-68f560f4790a4abab2c43fd861bc7808
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Reaction notes

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