Triethylamine → HCID 13733123, compound

HRID 360002Notes

Reaction equation

HRID 360002 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[CH2:3][CH2:4][NH2:5].C(N(CC)CC)C.[CH2:15]([C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1)[C:16]([CH3:19])([CH3:18])[CH3:17]>C(Cl)Cl.O>[CH3:1][C:2]([CH3:7])([CH3:6])[CH2:3][CH2:4][NH:5][C:24](=[O:25])[C:23]1[CH:27]=[CH:28][C:20]([CH2:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 197093,3-DimethylbutylamineHCID 151377194-(2,2-Dimethylpropyl)benzoyl chloride

Product 1

HCID 13733123HCID 13733123, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a cold solution of 5.26, g of 3,3-dimethylbutylamine and 21.0 ml of triethylamine in 180 ml of methylene chloride was added dropwise a solution of p-neopentylbenzoylchloride in 20 ml of methylene chloride. The resulting mixture was stirred at room temperature for 5 hours and diluted with water. The organic layer was washed with 3N hydrochloric acid, water, 1N sodium hydroxide, brine, dried, and evaporated to yield a solid. The solid was recrystallized from ethylacetate:hexane to yield N-(3,3-dimethylbutyl)-4-(2,2-dimethylpropyl)benzamide as a beige solid, mp 124°-126° C.

Workup

  1. washThe organic layer was washed with 3N hydrochloric acid, water, 1N sodium hydroxide, brine
  2. customdried
  3. customevaporated
  4. customto yield a solid
  5. customThe solid was recrystallized from ethylacetate

Sources & evidence

ORD record
ord-a685a34d690a4c55b169f61584d2543d
Source dataset
uspto-grants-1991_03
Patent number
US05003106

Reaction notes

Loading…