Trimethylamine → HCID 69017197, compound

HRID 1591598Notes

Reaction equation

HRID 1591598 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)C(O)=O.C(Cl)(=O)C(Cl)=[O:14].Cl.CNC.[CH3:22][N:23]([CH3:25])[CH3:24]>CN(C)C=O.ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[CH:6][C:10]=1[C:22]([N:23]([CH3:25])[CH3:24])=[O:14]

Participants

7

Reactant 4

HCID 1146TrimethylamineHCID 10473Dimethylamine, hydrochlorideHCID 65578Oxalyl chlorideHCID 820095-Chloro-2-methylbenzoic acid

Product 1

HCID 69017197HCID 69017197, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 5-chloro-2-methylbenzoic acid (10 g, 58.6 mmol) dichloromethane (100 ml), cooled in an ice bath, was added a solution of oxalyl chloride in dichloromethane (2 M, 33 ml, 66 mmol) followed by N,N-dimethylformamide (5 drops). After stirring for 2 hours, dimethylamine hydrochloride (9.5 g, 116 mmol) was added followed by a solution of trimethylamine (25 ml, 180 mmol) in dichloromethane (100 ml) slowly. After stirring for 3 hours, the mixture was concentrated under reduced pressure and partitioned between ethyl acetate (200 ml) and hydrochloric acid (1 M, 200 ml). The organic layer was concentrated under reduced pressure to afford 2-chloro-5, N,N,-trimethyl benzamide (11.6 g, 100% yield).

Workup

  1. temperaturecooled in an ice bath
  2. stirringAfter stirring for 3 hours
  3. concentrationthe mixture was concentrated under reduced pressure
  4. custompartitioned between ethyl acetate (200 ml) and hydrochloric acid (1 M, 200 ml)
  5. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ed9120b58cdf4628a02bf008b25dd771
Source dataset
uspto-grants-2007_11
Patent number
US07291616B2

Reaction notes

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