Hydrochloric Acid → 2-Chloro-3-fluoro-benzamidine

HRID 1804540Notes

Reaction equation

HRID 1804540 reaction equation
C[Si](C)(C)[N-:3][Si](C)(C)C.[Li+].[Cl:11][C:12]1[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:13]=1[C:14]#[N:15].Cl>CCCCCC.C(OCC)C>[Cl:11][C:12]1[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:13]=1[C:14]([NH2:3])=[NH:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 2733832Lithium HexamethyldisilazideHCID 37235862-Chloro-3-fluorobenzonitrile

Product 1

HCID 576985762-Chloro-3-fluoro-benzamidine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

320 ml (0.32 mmol) of a 1 molar solution of lithium hexamethyl disilazide (LiHMDS) in hexane are placed in 800 ml diethyl ether and combined at ambient temperature with 25.0 g (0.161) 2-chloro-3-fluoro-benzonitrile. The mixture is stirred for 2 h at ambient temperature and after cooling to 0° C. it is combined with 280 ml 3 normal hydrochloric acid. The precipitate formed is suction filtered, washed with water and dried.

Workup

  1. temperatureafter cooling to 0° C. it
  2. customThe precipitate formed
  3. filtrationfiltered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-8c300e53f2994e4a8d7fa6c0ef48ca95
Source dataset
uspto-grants-2013_01
Patent number
US08354418B2

Reaction notes

Loading…