Trimethylamine → HCID 21480500, compound

HRID 1490046Notes

Reaction equation

HRID 1490046 reaction equation
O[CH2:2][CH2:3][N:4]1[C:9]([CH2:10]O)=[CH:8][C:7]2[CH:12]=[CH:13][S:14][C:6]=2[S:5]1(=[O:16])=[O:15].CN(C)C.C1(C)C=CC(S([Cl:30])(=O)=O)=CC=1.[CH3:32][O:33][CH2:34][CH2:35][NH2:36].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[ClH:30].[CH3:32][O:33][CH2:34][CH2:35][N:36]1[CH2:2][CH2:3][N:4]2[S:5](=[O:16])(=[O:15])[C:6]3[S:14][CH:13]=[CH:12][C:7]=3[CH:8]=[C:9]2[CH2:10]1

Participants

7

Reactant 5

HCID 1146TrimethylamineHCID 73974-Toluenesulfonyl chlorideHCID 80182-MethoxyethylamineHCID 516892Sodium BicarbonateHCID 21480498HCID 21480498, compound

Product 1

HCID 21480500HCID 21480500, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product from Step D (1.37 g, 5.25 mmol and trimethylamine (2.12 g, 21.0 mmol) in methylene chloride (100 mL) at 0° C. was added p-toluenesulfonyl chloride (2.50 g, 13.13 mmol). The mixture was stirred for 3 h, cooled (about 7° C.) overnight, and 2-methoxyethylamine (5 mL) was added, followed by stirring for 2 h at ambient temperature and heating at reflux temperature for 2 h. A saturated solution of sodium bicarbonate (80 mL) was added to the reaction mixture which was extracted with ethyl acetate (2×80 mL). The combined extracts were evaporated to a residue which was purified by column chromatography (silica, ethyl acetate) to give a viscous oil (0.98 g, 62%). Dissolution of the oil in ethyl acetate (50 mL) and treatment with 2N HCl/EtOH (2 mL) provided a crystalline solid which was collected by filtration and dried to give a colorless solid: mp 208°-210° C.

Workup

  1. additionwas added
  2. stirringby stirring for 2 h at ambient temperature
  3. temperatureheating
  4. temperatureat reflux temperature for 2 h
  5. extractionwas extracted with ethyl acetate (2×80 mL)
  6. customThe combined extracts were evaporated to a residue which
  7. customwas purified by column chromatography (silica, ethyl acetate)

Sources & evidence

ORD record
ord-95ae2ed2b5c54fc0945aa5e2c5274729
Source dataset
uspto-grants-1997_10
Patent number
US05681834

Reaction notes

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