Hydrochloric Acid → 2-Chlorobenzimidamide
Reaction equation
C[Si](C)(C)[NH:3][Si](C)(C)C.C([Li])CCC.[Cl:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[C:18]#[N:19].Cl>C(OCC)C>[Cl:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[C:18](=[NH:3])[NH2:19]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
According to literature reference (Huang, Y.; Luedtke, R. R.; Freeman, R. A.; Wu, L.; Mach, R. H. Bioorg. Med. Chem. 2001, 9, 3113–3122), to a solution of hexamethyldisilazane (36.7 mL, 175 mmol) in of diethyl ether (300 mL) at 0° C. is added n-butyl lithium (114 mL of 1.6 M solution in hexanes, 182 mmol) and the reaction mixture is stirred at 0° C. for 30 minutes after which time 2-chlorobenzonitrile (10.0 grams, 72.7 mmol) is added and the reaction mixture is warmed to 25° C. and stirred for 5 hours. Once complete, the reaction is poured into 2 N HCl and the aqueous phase was washed twice with diethyl ether. This aqueous phase is then made basic (pH=12) by addition of 6N sodium hydroxide. Subsequently, the aqueous phase is extracted with CH2Cl2 and the combined organic extracts are dried over sodium sulfate and concentrated to provide a crude solid. The crude product is then recrystallized from ethyl acetate to afford 5.4 g of 2-chlorobenzenecarboximidamide.
Workup
- additionis added
- washthe aqueous phase was washed twice with diethyl ether
- additionby addition of 6N sodium hydroxide
- extractionSubsequently, the aqueous phase is extracted with CH2Cl2
- dry with materialthe combined organic extracts are dried over sodium sulfate
- concentrationconcentrated
- customto provide a crude solid
- customThe crude product is then recrystallized from ethyl acetate
Sources & evidence
- ORD record
- ord-4d78f933683144569a537d99b69f2b89
- Source dataset
- uspto-grants-2006_05
- Patent number
- US07041690B2
Reaction notes
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