Dimethylamine → HCID 59582127, compound

HRID 29713Notes

Reaction equation

HRID 29713 reaction equation
[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][NH:13][C:14]([C:16]2[O:17][C:18]3[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=3[C:20]=2[CH2:21]Br)=[O:15])=[CH:6][CH:5]=1.[CH3:28][NH:29][CH3:30].O1CCCC1>ClC1C=CC=CC=1.ClCCl>[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][NH:13][C:14]([C:16]2[O:17][C:18]3[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=3[C:20]=2[CH2:21][N:29]([CH3:30])[CH3:28])=[O:15])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 666882324-{2-[(3-Bromomethylbenzofuran-2-carbonyl)amino]ethoxy}benzoic acid methyl ester

Product 1

HCID 59582127HCID 59582127, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7964ChlorobenzeneSolvent

Procedure

A solution of 4-{2-[(3-bromomethylbenzofuran-2-carbonyl)amino]ethoxy}-benzoic acid methyl ester (0.340 mol) in chlorobenzene (200 ml) and dichloromethane (800 ml) was added dropwise to a 0-5° C. solution of 2M dimethylamine in tetrahydrofuran (510 ml, 1.022 mol) over 30 minutes with the temperature below 20° C. The resulting mixture was stirred for one hour and allowed to warm to ambient temperature. After completion of reaction, the reaction mixture was washed with 5% potassium carbonate and water. Solvent was distilled at atmospheric pressure until the pot temperature reached 100° C. After cooling to ˜50° C., acetonitrile (400 ml) and ethyl Acetate (400 ml) were added to the pot. The reaction mixture was heated to reflux until all solids dissolved. The reaction mixture was allowed to cool to give 4-{2-[(3-dimethylaminomethyl-benzofuran-2-carbonyl)amino]ethoxy}benzoic acid methyl ester (76.6 g) as an off white powder.

Workup

  1. customAfter completion of reaction
  2. washthe reaction mixture was washed with 5% potassium carbonate and water
  3. distillationSolvent was distilled at atmospheric pressure until the pot temperature
  4. customreached 100° C
  5. temperatureAfter cooling to ˜50° C.
  6. additionacetonitrile (400 ml) and ethyl Acetate (400 ml) were added to the pot
  7. temperatureThe reaction mixture was heated
  8. temperatureto reflux until all solids
  9. dissolutiondissolved
  10. temperatureto cool

Sources & evidence

ORD record
ord-6e7c4934695342f388ab2926659c498e
Source dataset
uspto-grants-2008_09
Patent number
US07420089B2

Reaction notes

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