4-Fluorobenzonitrile → 4-Fluorobenzamidine

HRID 239182Notes

Reaction equation

HRID 239182 reaction equation
[Li+].C[Si]([N-:6][Si](C)(C)C)(C)C.[F:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1.[OH-].[Na+]>CCCCCC.C(OCC)C>[F:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]([NH2:6])=[NH:17])=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 145174-FluorobenzonitrileHCID 14798Sodium HydroxideHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 42952384-Fluorobenzamidine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

380 mL 1N LiHMDS-solution in n-hexane was added to 20 g 4-fluoro-benzonitrile in 1 L diethylether. The reaction was stirred for 2 h at RT and decomposed with 1 L 4 NHCL-solution at 0° C. 4 N sodium hydroxide was added until pH 12 was reached and the water layer was extracted with chloroform. The organic layer was dried and evaporated to give 6.6 g of the desired product. Rt: 0.30 min (method B), (M+H)+: 139

Workup

  1. extractionthe water layer was extracted with chloroform
  2. customThe organic layer was dried
  3. customevaporated

Sources & evidence

ORD record
ord-c5046d2522ba4bd9ad006ba6e8a1ffe5
Source dataset
uspto-grants-2014_02
Patent number
US08642774B2

Reaction notes

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