Sodium Chloride → N'-(5-Amino-2-cyanophenyl)-N,N-dimethylformimidamide

HRID 249955Notes

Reaction equation

HRID 249955 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[CH:5][C:4]=1[N:12]=[CH:13][N:14]([CH3:16])[CH3:15])#[N:2].[OH-].[Na+].[Cl-].[Na+]>O1CCCC1.Cl.O.C(OCC)(=O)C.[Cl-].[Cl-].[Cl-].[Ti+3]>[NH2:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[C:4]([N:12]=[CH:13][N:14]([CH3:15])[CH3:16])[CH:5]=1

Participants

9

Reactant 3

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 67128670N'-(2-Cyano-5-nitrophenyl)-N,N-dimethylformimidamide

Product 1

HCID 57787953N'-(5-Amino-2-cyanophenyl)-N,N-dimethylformimidamideYield 73%

Reagents, catalysts & solvents 5

HCID 10313229titanium(III) trichlorideCatalystHCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

N′-(2-Cyano-5-nitrophenyl)-N,N-dimethylformimidamide (1.0 g, 4.58 mmol) is dissolved in 100 mL of tetrahydrofuran, cooled to 0° C. and admixed with titanium trichloride solution (69 mL of a 15% solution in 10% aqueous HCl). Then, the batch is stirred at room temperature for 4 hours and adjusted at 0° C. to pH 9 with 2N aqueous sodium hydroxide solution. The mixture is diluted with water and ethyl acetate. The aqueous phase is saturated with sodium chloride and stirred out three times with ethyl acetate. The combined organic phases are dried over sodium sulphate. Removal of the solvent and also chromatographic purification (silica gel, n-hexane/ethyl acetate:→100% ethyl acetate) gives the desired product in 73% yield (630 mg).

Workup

  1. dry with materialThe combined organic phases are dried over sodium sulphate
  2. customRemoval of the solvent and also chromatographic purification (silica gel, n-hexane/ethyl acetate:→100% ethyl acetate)

Sources & evidence

ORD record
ord-177738f12a3749e696043d9eb81a9c77
Source dataset
uspto-grants-2011_01
Patent number
US07863283B2

Reaction notes

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