Nitrobenzene → HCID 178458251, compound

HRID 1858023Notes

Reaction equation

HRID 1858023 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[NH2:12])[C:6]([NH2:8])=[NH:7].[N+:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([O-])=O.[C:22](#N)[CH3:23].C[CH2:26][O:27]CC>>[CH2:26]([O:27][C:21]1[CH:20]=[CH:19][C:18]([C:17]2[NH:12][C:11]3[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[NH:7])=[CH:4][C:3]=3[N:2]=2)=[N:13][CH:16]=1)[CH2:22][CH3:23]

Participants

4

Reactant 3

HCID 7416NitrobenzeneHCID 21885917Acetonitrile etherHCID 221255323,4-Diaminobenzimidamide hydrochloride

Product 1

HCID 178458251HCID 178458251, compound

Procedure

A mixture comprising 5-propoxypyridine-2-carboxyaldehyde (0.19 g, 1.15 mmol), 3,4-diaminobenzamidine hydrochloride (0.21 g, 1.15 mmol) and nitrobenzene (2 mL) was heated at 150° C. for 15 hours, cooled and then diluted with 1:1 acetonitrile/ether (50 mL) to give a precipitate. The precipitate was isolated by filtration and purified by HPLC to provide 2-(5-propyloxypyridin-2-yl]-1H-benzimidazole-5-carboxamidine. 1H-NMR (300 Mhz, CD3OD): 1.1 (t, 3H), 2.0 (m, 2H), 4.5 (t, 2H), 7.75 (m, 1H), 7.86 (m, 2H), 8.1 (m, 1H), 8.35 (m, 1H); 8.55 (m, 1H); MS (ESI), Calculated for C16H17N5O: 295.3, Found (MH+): 295.9.

Workup

  1. temperaturecooled
  2. customto give a precipitate
  3. customThe precipitate was isolated by filtration
  4. custompurified by HPLC

Sources & evidence

ORD record
ord-fc682aa69d8f4f1c8e6e41ff40afcd5a
Source dataset
uspto-grants-2000_11
Patent number
US06150379

Reaction notes

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