Sodium Hydroxide → HCID 21409814, compound

HRID 1283558Notes

Reaction equation

HRID 1283558 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5](Cl)=[O:6].[CH3:12][C:13]([N:20]([CH3:22])[CH3:21])([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:14][NH2:15].[OH-].[Na+]>C1C=CC=CC=1.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([NH:15][CH2:14][C:13]([CH3:12])([N:20]([CH3:22])[CH3:21])[CH2:16][CH2:17][CH2:18][CH3:19])=[O:6]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 76403Benzoyl chloride, 3,4-dichloro-HCID 53989671HCID 53989671, compound

Product 1

HCID 21409814HCID 21409814, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 962WaterSolvent

Procedure

A solution of 3,4-dichlorobenzoyl chloride (2.1 g.,) in dry benzene (25 ml.) was added to a solution of 2-methyl-2-dimethylamino-hexylamine (1.58 g.,) in dry benzene (25 ml.) and the mixture heated under reflux for 1.5 hrs.. The mixture was diluted with water, basified with 2N sodium hydroxide solution, and extracted with benzene (4 × 100 ml.). The combined benzene extracts were washed with water (4 × 50 ml.), dried (Na2SO4) and evaporated affording 3,4-dichloro-N-[2-methyl-2-dimethylamino-hexyl]benzamide as a colourless oil (3.6 g., ca 100%) which slowly crystallised.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 1.5 hrs
  3. extractionextracted with benzene (4 × 100 ml.)
  4. washThe combined benzene extracts were washed with water (4 × 50 ml.)
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-7e00a6cc2bf1453885867e91c6f4b0cb
Source dataset
uspto-grants-1976_08
Patent number
US03975443

Reaction notes

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