Hydrochloric Acid → 4-Fluorobenzamidine

HRID 1896153Notes

Reaction equation

HRID 1896153 reaction equation
C[Si](C)(C)[NH:3][Si](C)(C)C.[Li]CCCC.[F:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=1.Cl>CCOCC>[F:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]([NH2:3])=[NH:21])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 13838HexamethyldisilazaneHCID 145174-FluorobenzonitrileHCID 178418339Butyllithium

Product 1

HCID 42952384-Fluorobenzamidine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To an ice-cold solution of hexamethyldisilazane (7 mL) in Et2O (40 mL) was added n-BuLi (1.6M in hexanes, 20.6 mL), followed by a solution of 4-fluorobenzonitrile (2 g) in Et2O (10 ml). After stirring at 0° C. for 10 min, the mixture was allowed to warm to RT and was stirred at RT for 20 h. The mixture was acidified to pH 1 by adding a 1M HCl solution and was washed with CHCl3. The aq. layer was then basified to pH 14 by adding Na2CO3 and NaOH and was extracted twice with CHCl3. The org. layers were dried (Na2SO4) and evaporated off to afford the desired compound (1.59 g).

Workup

  1. temperatureto warm to RT
  2. stirringwas stirred at RT for 20 h
  3. washwas washed with CHCl3
  4. additionby adding Na2CO3 and NaOH
  5. extractionwas extracted twice with CHCl3
  6. dry with materiallayers were dried (Na2SO4)
  7. customevaporated off

Sources & evidence

ORD record
ord-44369cdf8d95406aa7deddfaa1cb4985
Source dataset
uspto-grants-2013_08
Patent number
US08518912B2

Reaction notes

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