Potassium Hydroxide → 4-choro-N-[4-(diethylamino)-1-methylbutyl]-2-nitrobenzamide

HRID 261899

Reaction equation

HRID 261899 reaction equation
[CH2:1]([N:3]([CH2:10][CH3:11])[CH2:4][CH2:5][CH2:6][CH:7]([NH2:9])[CH3:8])[CH3:2].[Cl:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[C:15]([N+:22]([O-:24])=[O:23])[CH:14]=1.[OH-].[K+]>O.ClCCCl>[Cl:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([NH:9][CH:7]([CH3:8])[CH2:6][CH2:5][CH2:4][N:3]([CH2:1][CH3:2])[CH2:10][CH3:11])=[O:18])=[C:15]([N+:22]([O-:24])=[O:23])[CH:14]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 78953NovoldiamineHCID 108677844-Chloro-2-nitrobenzoyl chloride

Product 1

HCID 131010514-choro-N-[4-(diethylamino)-1-methylbutyl]-2-nitrobenzamide

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 962WaterSolvent2×

Procedure

To a vigorously stirred mixture containing 970 g. (6.2 moles) of freshly distilled N1,N1 -diethyl-1,4 pentanediamine, 4 l. of 1,2-dichloroethane and 1 l. of water at 5°-10° C. there was simultaneously added dropwise a solution containing 5.95 moles of 4-chloro-2-nitrobenzoyl chloride in approximately 8 l. of 1,2-dichloroethane and a solution containing 410 g. (6.2 moles) of 85% potassium hydroxide in 1 l. of water. When the addition was complete the ice bath was removed and stirring was continued 0.5 hours at room temperature. The organic layer was separated, dried over anhydrous calcium sulfate and evaporated to dryness under vacuum. The residue was dissolved in 3 l. or 1,2-dichloroethane and the resulting solution was treated with decolorizing carbon and filtered. The filtrate was diluted to 6 l. with additional 1,2-dichloroethane to give a pale yellow solution of 4-choro-N-[4-(diethylamino)-1-methylbutyl]-2-nitrobenzamide which was divided into three equal portions which were used directly in the next step.

Workup

  1. additionTo a vigorously stirred mixture containing 970 g
  2. additionWhen the addition
  3. customwas removed
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous calcium sulfate
  6. customevaporated to dryness under vacuum
  7. dissolutionThe residue was dissolved in 3 l
  8. additionor 1,2-dichloroethane and the resulting solution was treated with decolorizing carbon
  9. filtrationfiltered
  10. additionThe filtrate was diluted to 6 l

Sources & evidence

ORD record
ord-d83532fc3e954dd1be6dfdee0defb5ab
Source dataset
uspto-grants-1979_05
Patent number
US04152518

Linked notes

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