Sodium Hydroxide → HCID 21409814, compound

HRID 2072014Notes

Reaction equation

HRID 2072014 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-cbb12cc2c247492a8eb8830d0fc1f6e6
Source dataset
uspto-grants-1977_09
Patent number
US04049663

Reaction notes

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