Benzylethanolamine → HCID 68578657, compound

HRID 886838Notes

Reaction equation

HRID 886838 reaction equation
[Br:1][C:2]1[C:3]([F:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.CN(C)C=O.[CH2:17]([NH:24][CH2:25][CH2:26][OH:27])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C>S(Cl)(Cl)=O.O1CCCC1.O>[CH2:17]([N:24]([CH2:25][CH2:26][OH:27])[C:5](=[O:7])[C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([Br:1])[C:3]=1[F:11])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

8

Reactant 4

HCID 4348BenzylethanolamineHCID 6228DimethylformamideHCID 8471TriethylamineHCID 27363133-Bromo-2-fluorobenzoic acid

Product 1

HCID 68578657HCID 68578657, compoundYield 71.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 3-bromo-2-fluorobenzoic acid (10.0 g, 45.9 mmol) and N,N-dimethylformamide (0.100 ml) in thionylchloride (10 ml) was stirred for 3 hr at 85° C., and the solvent was evaporated under reduced pressure. The residue was added to a solution of N-benzylethanolamine (6.94 g, 45.8 mmol) and triethylamine (9.60 ml, 68.9 mmol) in tetrahydrofuran (140 ml) under ice-cooling, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give the desired product (11.5 g, 68.9%) as an oil.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. temperaturecooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-3d737f8f1dfa4088956047a8242b7c00
Source dataset
uspto-grants-2012_08
Patent number
US08247403B2

Reaction notes

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