Methanol → HCID 86756047, compound

HRID 1858022Notes

Reaction equation

HRID 1858022 reaction equation
[CH2:1]([C:5]1[CH:6]=[CH:7][C:8](C(O)=O)=[N:9][CH:10]=1)[CH2:2][CH2:3][CH3:4].Cl.[NH2:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][C:24]=1[NH2:25])[C:19]([NH2:21])=[NH:20].O.[OH-].[Na+].[CH3:29]O>C(OCC)(=O)C.CCOCC.CC(C)=O>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([N:25]2[C:24]3[CH:23]=[CH:22][C:18]([C:19]([NH2:21])=[NH:20])=[CH:17][C:16]=3[N:15]=[CH:29]2)=[N:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

9

Reactant 5

HCID 887MethanolHCID 962WaterHCID 3442Fusaric AcidHCID 14798Sodium HydroxideHCID 221255323,4-Diaminobenzimidamide hydrochloride

Product 1

HCID 86756047HCID 86756047, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture comprising 5-butylpyridine-2-carboxylic acid (4 g, 22.3 mmol), 3,4-diaminobenzamidine hydrochloride (3.8 g, 20.1 mmol) and polyphosphoric acid (15 mL) was heated at 185° C. for 2.5 hours, cooled and then poured into water (100 mL). The mixture was cooled to 0° C. and neutralized with 50% sodium hydroxide to give a precipitate. The precipitate was isolated by filtration, washed with water and stirred with saturated sodium bicarbonate solution for 30 minutes. The precipitate was again isolated by filtration, washed with water and dissolved in 6N hydrochloric acid (40 mL). The solution was poured into stirring acetone (4 mL) to give a precipitate. The precipitate was dissolved in hot methanol (30 mL) and the solution was diluted sequentially with ethyl acetate (50 mL), ether (200 mL) and acetone (100 mL) to give a tan precipitate. The precipitate was isolated by filtration, washed with acetone (200 mL) and dried to provide 2-(5-butylpyridin-2-yl-1H-benzimidazole-5-carboxamidine (3.45 g, 11.8 mmol). 1H-NMR (300 Mhz, DMSO-d6): 0.8 (m, 3H), 1.3 (m, 2H), 1.6 (m, 2H), 2.7 (m, 2H), 7.85 (m, 2H), 7.97 (dd, 1H, J=8.1 Hz, 1.5 Hz), 8.23 (s, 1H), 8.55 (d, 1H, J=8.1 Hz), 8.69 (d, 1H, J=1.5 Hz); MS (ESI); Calculated for C17H19N5 : 293.3; Found (MH+): 294.1.

Workup

  1. temperaturecooled
  2. customto give a precipitate
  3. customThe precipitate was isolated by filtration
  4. washwashed with water
  5. customThe precipitate was again isolated by filtration
  6. washwashed with water
  7. dissolutiondissolved in 6N hydrochloric acid (40 mL)
  8. additionThe solution was poured
  9. stirringinto stirring acetone (4 mL)
  10. customto give a precipitate
  11. customto give a tan precipitate
  12. customThe precipitate was isolated by filtration
  13. washwashed with acetone (200 mL)
  14. customdried

Sources & evidence

ORD record
ord-cddb09076be448d48d045d8ae73f9269
Source dataset
uspto-grants-2000_11
Patent number
US06150379

Reaction notes

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