Benzoyl chloride, 3,4-dichloro- → HCID 21409836, compound

HRID 1283560Notes

Reaction equation

HRID 1283560 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][NH:13][CH2:14][C:15]([CH3:23])([N:20]([CH3:22])[CH3:21])[CH2:16][CH2:17][CH2:18][CH3:19]>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([N:13]([CH3:12])[CH2:14][C:15]([CH3:23])([N:20]([CH3:21])[CH3:22])[CH2:16][CH2:17][CH2:18][CH3:19])=[O:6]

Participants

4

Reactant 2

HCID 76403Benzoyl chloride, 3,4-dichloro-HCID 21409919HCID 21409919, compound

Product 1

HCID 21409836HCID 21409836, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 3,4-dichlorobenzoyl chloride (1.048 g., 5 mmole) in dry benzene (25 ml.) was added to a solution of N-methyl-2-methyl-2-dimethylamino hexylamine (0.754 g., 4.4 mmole) in dry benzene (25 ml.) and the solution heated under reflux for 1 hr.. The cooled solution was washed with 2N sodium hydroxide solution (4 × 100 ml.), water (4 × 100 ml.), dried (Na2SO4) and evaporated to a colourless oil (1.612 g.). The oil was dissolved in benzene, chromatographed on a column of alumina (25 × 3.0 cm.) eluting with benzene/ether 1:1, and fractions (9 × 100 ml.) were collected. Fractions 2-8 were combined and, on evaporation, afforded 3,4-dichloro-N-methyl-N-[2-methyl-2-dimethylamino-hexyl]benzamide as a colourless oil (1.282 g., 84%).

Workup

  1. temperaturethe solution heated
  2. temperatureunder reflux for 1 hr
  3. washThe cooled solution was washed with 2N sodium hydroxide solution (4 × 100 ml.), water (4 × 100 ml.)
  4. dry with materialdried (Na2SO4)
  5. customevaporated to a colourless oil (1.612 g.)
  6. dissolutionThe oil was dissolved in benzene
  7. customchromatographed on a column of alumina (25 × 3.0 cm.)
  8. washeluting with benzene/ether 1:1, and fractions (9 × 100 ml.)
  9. customwere collected
  10. customFractions 2-8 were combined and, on evaporation

Sources & evidence

ORD record
ord-c6dcae0e61e049daa9976915b06c5475
Source dataset
uspto-grants-1976_08
Patent number
US03975443

Reaction notes

Loading…