Dimethylamine → HCID 21196241, compound

HRID 1066827Notes

Reaction equation

HRID 1066827 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4](O)=[O:5].C(Cl)(=O)C(Cl)=O.[CH3:18][NH:19][CH3:20]>C(Cl)Cl.CN(C)C=O>[CH3:18][N:19]([CH3:20])[C:4](=[O:5])[C:3]1[CH:7]=[C:8]([Br:11])[CH:9]=[CH:10][C:2]=1[F:1]

Participants

6

Reactant 3

HCID 674DimethylamineHCID 65578Oxalyl chlorideHCID 27363155-Bromo-2-fluorobenzoic acid

Product 1

HCID 21196241HCID 21196241, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 2-fluoro-5-bromobenzoic acid (680 mg, 3.10 mmol) in methylene chloride (20 ml) was treated with oxalyl chloride (0.35 ml, 4.04 mmol), followed by four drops of N,N-dimethylformamide. The resulting clear solution was stirred for about three hours. The solvents were removed in vacuo and the residue was redissolved in methylene chloride and treated with dimethylamine (4.6 ml, 9.3 mmol). Stirring was continued for 18 hours. The reaction mixture was diluted with methylene chloride, and washed with saturated sodium bicarbonate and brine. The organic fraciton was dried over sodium sulfate, and the solvents were removed in vacuo. The desired title product was further purified by liquid chromatography.

Workup

  1. customThe solvents were removed in vacuo
  2. dissolutionthe residue was redissolved in methylene chloride
  3. stirringStirring
  4. waitwas continued for 18 hours
  5. washwashed with saturated sodium bicarbonate and brine
  6. dry with materialThe organic fraciton was dried over sodium sulfate
  7. customthe solvents were removed in vacuo
  8. customThe desired title product was further purified by liquid chromatography

Sources & evidence

ORD record
ord-0dd86a7711074aeeab49e7d270a5b378
Source dataset
uspto-grants-2001_06
Patent number
US06245761B1

Reaction notes

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