HCID 53945300, compound → HCID 178488921, compound

HRID 841534Notes

Reaction equation

HRID 841534 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:) δ7.07 (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-de421412bb634f078d67c8d098d88ad1
Source dataset
uspto-grants-2002_04
Patent number
US06369235B1

Reaction notes

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