Ethyl 2-chloroethanecarboximidate hydrochloride → 1-n-Propyl-2-chloromethyl-5-cyanobenzimidazole hydrochloride

HRID 1594039Notes

Reaction equation

HRID 1594039 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[NH:10][CH2:11][CH2:12][CH3:13])[C:5]#[N:6].Cl.[Cl:15][CH2:16][C:17](=N)OCC>C(O)C>[ClH:15].[CH2:11]([N:10]1[C:9]2[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=2[N:1]=[C:17]1[CH2:16][Cl:15])[CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 12470659Ethyl 2-chloroethanecarboximidate hydrochlorideHCID 223802993-Amino-4-(propylamino)benzonitrile

Product 1

HCID 223800631-n-Propyl-2-chloromethyl-5-cyanobenzimidazole hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-amino-4-n-propylaminobenzonitrile (7.38 g, 42.1 mmol) and ethyl chloroacetimidate hydrochloride (9.92 g, 63.2 mmol) in ethanol (100 mL) is heated at reflux for 17 h, then cooled and concentrated to give 1-n-Propyl-2-chloromethyl-5-cyanobenzimidazole hydrochloride. Prior to use in the next step, this material is converted to free base by adding aqueous bicarbonate and extracting with dichloromethane, drying (Na2SO4), and concentrating.

Workup

  1. temperatureat reflux for 17 h
  2. temperaturecooled
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0511a317f3874bd9a5543de48b39c50a
Source dataset
uspto-grants-2007_11
Patent number
US07300945B2

Reaction notes

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