Dimethylformamide → Dichlorobenzylidenamine

HRID 1350911Notes

Reaction equation

HRID 1350911 reaction equation
Cl.[Cl:2]CCC(N)(C)C.[Cl:9][C:10]1[CH:17]=[CH:16][CH:15]=[C:14](Cl)[C:11]=1C=O.C[N:20]([CH3:23])C=O>C1(C)C=CC=CC=1.C(C(OC(CC)(CC)C)(CC)C)C.O1CCCC1.CS(C)=O.C(Cl)Cl>[Cl:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[C:23]([Cl:2])=[NH:20]

Participants

9

Reactant 3

HCID 6228DimethylformamideHCID 67372,6-DichlorobenzaldehydeHCID 210945474-Chloro-2-methylbutan-2-amine hydrochloride

Product 1

HCID 131726441Dichlorobenzylidenamine

Reagents, catalysts & solvents 5

HCID 679Dimethyl SulfoxideSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 12430074DiethylethyletherSolvent

Procedure

The base is liberated from about 80–90, preferably 84.0 mmol of 3-chloro-1,1-dimethylpropylamine-hydrochloride by known methods. The free base is dissolved in about 50 mL of a solvent, preferably toluene, diethylethylether, tetrahydrofuran, dimethylsulphoxide, dimethylformamide or methylene chloride and about 60 to 100 mmol, preferably 80.0 mmol of 2,6-dichlorobenzaldehyde are added at ambient temperature, with stirring. The reaction mixture is stirred for 5 to 20 h, preferably for 15 h at ambient temperature, dried again and the solvent is removed. The corresponding dichlorobenzylidenamine of compound (III) is obtained.

Workup

  1. additionare added at ambient temperature
  2. stirringThe reaction mixture is stirred for 5 to 20 h, preferably for 15 h at ambient temperature
  3. customdried again
  4. customthe solvent is removed

Sources & evidence

ORD record
ord-6af98bf814c24801a9689cef8d7e3e26
Source dataset
uspto-grants-2007_05
Patent number
US07214698B2

Reaction notes

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