4-Fluorobenzonitrile → 4-Fluorobenzamidine

HRID 336370Notes

Reaction equation

HRID 336370 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>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

5

Reactant 2

HCID 145174-FluorobenzonitrileHCID 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 2 h at RT and 4N HCL solution was added at 0° C. until pH=12. The water layer was extracted with chloroform. The organic layer was dried and evaporated to give 6.64 g of the desired product. Rt: 2.28 min (method K), (M+H)+: 139

Workup

  1. addition4N HCL solution was added at 0° C. until pH=12
  2. extractionThe water layer was extracted with chloroform
  3. customThe organic layer was dried
  4. customevaporated

Sources & evidence

ORD record
ord-86a9286ea88c4f02aaaf771257efd45d
Source dataset
uspto-grants-2014_11
Patent number
US08889677B2

Reaction notes

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