Hydrochloric Acid → 3-Methoxy-4-nitrobenzimidamide

HRID 2112099Notes

Reaction equation

HRID 2112099 reaction equation
[Li].C[Si]([N-:6][Si](C)(C)C)(C)C.[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[N+:21]([O-:23])=[O:22])[C:16]#[N:17].Cl>C1COCC1>[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[N+:21]([O-:23])=[O:22])[C:16]([NH2:6])=[NH:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 108992273-Methoxy-4-nitrobenzonitrileHCID 86605622Lithium bistrimethylsilylamide

Product 1

HCID 187277063-Methoxy-4-nitrobenzimidamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
10 °C

Procedure

99 ml (99 mmol) lithium-bis-trimethylsilylamide solution (1 mol/l in THF) are diluted with 640 ml THF, cooled to 10° C. and combined with 8.3 g (46.591 mmol) 3-methoxy-4-nitro-benzonitrile. The reaction mixture is stirred for 10 min at 20° C. The mixture is cooled to 0° C. and combined with 80 ml 3 N hydrochloric acid. The reaction mixture is evaporated down in vacuo and extracted with water and ethyl acetate. The aqueous phase is adjusted to pH 14 with 3 N sodium hydroxide solution. The product is then suction filtered.

Workup

  1. temperatureThe mixture is cooled to 0° C.
  2. customThe reaction mixture is evaporated down in vacuo
  3. extractionextracted with water and ethyl acetate
  4. filtrationsuction filtered

Sources & evidence

ORD record
ord-03f878d92c30423e94aeef6bbc6ae4e5
Source dataset
uspto-grants-2009_04
Patent number
US07521457B2

Reaction notes

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