Ammonia → 1-Isopropyl-4-iodo-5-aminobenzimidazole

HRID 2299130Notes

Reaction equation

HRID 2299130 reaction equation
[CH:1]([N:4]1[C:8]2[CH:9]=[CH:10][C:11]([NH2:13])=[CH:12][C:7]=2[N:6]=[CH:5]1)([CH3:3])[CH3:2].[I:14]I.N.CO.C(Cl)Cl>CC(O)=O.[Hg](OC(C)=O)OC(C)=O>[CH:1]([N:4]1[C:8]2[CH:9]=[CH:10][C:11]([NH2:13])=[C:12]([I:14])[C:7]=2[N:6]=[CH:5]1)([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 807IodineHCID 162441621-Isopropyl-1H-benzoimidazol-5-ylamineHCID 21226129Dichloromethane methanol

Product 1

HCID 183798521-Isopropyl-4-iodo-5-aminobenzimidazoleYield 35%

Reagents, catalysts & solvents 2

HCID 16683746DiacetyloxymercuryCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 1-isopropyl-5-aminobenzimidazole (0.70 g, 3.7 mmol) and Hg(OAc)2 (2.1 g, 5.6 mmol) in 10 ml of AcOH was added solution of I2 in ACOH until it produces a precipitation; The reaction mixture was concentrated in vacuo to provide a brown solid which was subjected to column chromatography (5% NH3 sat'd MeOH/CH2Cl2) to provide 0.40 g (1.3 mmol, 35%) of the product.

Workup

  1. customproduces
  2. customa precipitation
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customto provide a brown solid which

Sources & evidence

ORD record
ord-6784b1776ddb4dacb3a23f00c9116701
Source dataset
uspto-grants-2002_12
Patent number
US06495583B1

Reaction notes

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