Dimethylamine → 2-chloro-4,5-difluoro-N,N-dimethylbenzamide

HRID 20598

Reaction equation

HRID 20598 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4](O)=[O:5].Cl[C:14]([N:18](C)[CH3:19])=C(C)C.C(N(CC)CC)C.CNC.C1COCC1>C(Cl)Cl.Cl>[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4]([N:18]([CH3:19])[CH3:14])=[O:5]

Participants

8

Reactant 5

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 7371712-Chloro-4,5-difluorobenzoic acid

Product 1

HCID 593469042-chloro-4,5-difluoro-N,N-dimethylbenzamideYield 96.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-chloro-4,5-difluorobenzoic acid (385 mg, 2.0 mmol) in DCM (5 mL) was treated with (1-chloro-2-methylprop-1-en-1-yl)dimethylamine (293 mg, 2.2 mmol) and stirred under argon for 1 hour. The mixture was then treated with triethylamine (0.56 mL, 4.0 mmol) and a 2M solution of dimethylamine in THF (1.2 mL, 2.4 mmol), and stirred for 18 hours. The mixture was diluted with DCM (5 mL) and 2M hydrochloric acid (4 mL) and separated. The organic layer was dried (MgSO4), filtered and concentrated in vacuo to afford the title compound (425 mg). The residue was used without further purification.

Workup

  1. customseparated
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-29d4985e8b5643428721490fac721520
Source dataset
uspto-grants-2010_06
Patent number
US07745475B2

Linked notes

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