Triethylamine → 4-iodo-N,N-dimethylbenzamide

HRID 230612Notes

Reaction equation

HRID 230612 reaction equation
Cl.[CH3:2][NH:3][CH3:4].C(N(CC)CC)C.[I:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=1>ClCCl>[I:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([N:3]([CH3:4])[CH3:2])=[O:18])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 743734-Iodobenzoyl chloride

Product 1

HCID 8799334-iodo-N,N-dimethylbenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of dimethylamine hydrochloride (2.45 g, 30 mmol) in dichloromethane (150 ml) was cooled in an ice/methanol bath and then treated with triethylamine (6.0 g, 59 mmol) followed by 4-iodobenzoyl chloride (8.0 g, 30 mmol) portionwise with stirring under an atmosphere of argon. The reaction mixture was allowed to stir at room temperature for 30 minutes before the solution was washed with water (2×100 ml). The organic layer was separated, dried over sodium sulphate, and evaporated under reduced pressure to give the title compound as a light beige coloured solid (7.73 g, 94%).

Workup

  1. temperaturewas cooled in an ice/methanol bath
  2. stirringto stir at room temperature for 30 minutes before the solution
  3. washwas washed with water (2×100 ml)
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulphate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-254dea5b0d9a420fa7f12f1c1270b4a9
Source dataset
uspto-grants-2009_07
Patent number
US07566735B2

Reaction notes

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