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Hydrochloric Acid → (E)-2-(3,3-Dimethyl-1-butenyl)-1-(2-pyridyl)-1H-benzimidazole hydrochloride

HRID 50902
Notes
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Reaction equation

HRID 50902 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH2:14].[CH3:15][C:16]([CH3:23])([CH3:22])/[CH:17]=[CH:18]/[C:19]([Cl:21])=O.N1C=CC=CC=1N1C2C=CC=CC=2N=C1/C=C/C1C=CC=CC=1.Cl>CO>[ClH:21].[CH3:15][C:16]([CH3:23])([CH3:22])/[CH:17]=[CH:18]/[C:19]1[N:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:14]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 752150N1-(pyridin-2-yl)benzene-1,2-diamineHCID 9796241(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazoleHCID 22736682(E)-4,4-dimethyl-2-pentenoyl chloride

Product 1

HCID 22736720(E)-2-(3,3-Dimethyl-1-butenyl)-1-(2-pyridyl)-1H-benzimidazole hydrochloride

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Procedure

To a solution of (E)-4,4-dimethyl-2-pentenoic acid (Gream, G. E.; Serelis, A. K. Aust. J. Chem. 1978, 31, 863) (200 mg, 1.6 mmol) in benzene (10 ml) was added thionyl chloride (0.5 ml) and the mixture was heated to reflux for 60 min. Volatiles were removed by evaporation to give crude (E)-4,4-dimethyl-2-pentenoyl chloride. Free base of the titled compound was prepared from N-(2-pyridyl)-o-phenylenediamine (150 mg, 0.81 mmol) and (E)-4,4-dimethyl-2-pentenoyl chloride obtained as above according to the preparation of (E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole (Example 1, method A). The free base was dissolved with a 10% methanol solution of hydrogen chloride (5 ml). Concentration and recrystallization from ethyl acetate yielded the titled compound. MW: 313.83; mp: 171.0-172.3° C.; 1H-NMR (CDCl3) δ: 8.86-8.82 (1H, m), 8.27 (1H, d, J=16.3 Hz), 8.21-8.13 (2H, m), 7.72-7.65 (1H, m), 7.62-7.43 (4H, m), 6.31 (1H, d, J=16.3 Hz), 1.17 (9H, s).

Workup

  1. customobtained as
  2. concentrationConcentration and recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-91ccf9cc97df4d43a03843bc3c7d34f0
Source dataset
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06713482B2

Reaction notes

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