Triethylamine → HCID 66688964, compound

HRID 1020393Notes

Reaction equation

HRID 1020393 reaction equation
[Br:1][C:2]1[C:3]([CH2:16]Br)=[C:4]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:5]([O:7]C)=O.Cl.[NH2:19][CH2:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=1.C(N(CC)CC)C>C1COCC1>[Br:1][C:2]1[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[CH:9]=[C:4]2[C:3]=1[CH2:16][N:19]([CH2:20][C:21]1[CH:22]=[CH:23][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:29][CH:30]=1)[C:5]2=[O:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2729253Methyl 4-(aminomethyl)benzoate hydrochlorideHCID 72942195HCID 72942195, compound2×

Product 1

HCID 66688964HCID 66688964, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-bromo-2-(bromomethyl)-4,5-dimethoxybenzoate (1.5 g, 4.1 mmol) and methyl 4-(aminomethyl)benzoate hydrochloride (1.6 g, 2 equiv.) in the step 1 were dissolved in a mixture of THF and distilled water (mixture ratio=4:1 (v/v), 10 mL). Triethyl amine (1.7 mL, 3 equiv.) was added thereto and stirred at room temperature for 1 night. The reaction proceeded until no methyl 3-bromo-2-(bromomethyl)-4,5-dimethoxybenzoate was detectable by thin-layer chromatography (TLC). The resulting mixture thus obtained was distilled under a reduced pressure to remove THF. The resulting material was dissolved in ethyl acetate and washed with saturated sodium bicarbonate solution and the distilled water. The isolated organic layer was collected, dried over anhydrous MgSO4, and distilled under a reduced pressure to remove solvent. The resulting residue was subjected to a silica gel column chromatography (EtOAc/hexane=1:1) to obtain the title compound (1.6 g, 93%).

Workup

  1. distillationdistilled water (mixture ratio=4:1 (v/v), 10 mL)
  2. customThe resulting mixture thus obtained
  3. distillationwas distilled under a reduced pressure
  4. customto remove THF
  5. dissolutionThe resulting material was dissolved in ethyl acetate
  6. washwashed with saturated sodium bicarbonate solution
  7. customThe isolated organic layer was collected
  8. dry with materialdried over anhydrous MgSO4
  9. distillationdistilled under a reduced pressure
  10. customto remove solvent

Sources & evidence

ORD record
ord-65fdfed040cb4b17af376c6b16dc4b4b
Source dataset
uspto-grants-2014_05
Patent number
US08716326B2

Reaction notes

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