HCID 53945300, compound → HCID 178488921, compound

HRID 2182087Notes

Reaction equation

HRID 2182087 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-])=O)[C:4]=1[NH:12][C:13]([CH:15]1[CH2:17][CH2:16]1)=O>C(O)(=O)C.[Fe]>[CH:15]1([C:13]2[NH:12][C:4]3[C:3]([O:2][CH3:1])=[CH:8][CH:7]=[CH:6][C:5]=3[N:9]=2)[CH2:17][CH2:16]1

Participants

4

Reactant 1

HCID 53945300HCID 53945300, compound

Product 1

HCID 178488921HCID 178488921, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

Cyclopropanecarboxylic acid (2-methoxy-6-nitro-phenyl)-amide (5013) (7.80 g, 33.1 mmol) and iron powder (7.60 g) were suspended in acetic acid (200 mL) for 25 min at reflux. The reaction was concentrated and redissolved in ethyl acetate, and washed with NaHCO3 (sat. aq) and NaCl (sat. aq). The combined washings were dried (Na2SO4), filtered and concentrated. The crude product was purified by flash chromatography with 2% MeOH/CH2Cl2 and recrystallization from diethyl ether/hexane (3:1), yielding white crystals of 2-(cyclopropyl)-4-methoxylbenzimidazole (5014) (4.90 g, 26.1 mmol, 79% yield). 1H-NMR (200 MHz, CD2Cl2:) δ 7.07 (cm, 2H), 6.65 (cm, 1H), 3.90 (s, 3H, OCH3), 2.17-2.03 (m, 1H), 1.22-0.96 (m, 4H).

Workup

  1. temperatureat reflux
  2. concentrationThe reaction was concentrated
  3. dissolutionredissolved in ethyl acetate
  4. washwashed with NaHCO3 (sat. aq) and NaCl (sat. aq)
  5. dry with materialThe combined washings were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by flash chromatography with 2% MeOH/CH2Cl2 and recrystallization from diethyl ether/hexane (3:1)

Sources & evidence

ORD record
ord-63993bb54bdf4550b29c77a226c212c4
Source dataset
uspto-grants-2005_05
Patent number
US06894068B2

Reaction notes

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