Triethylamine → HCID 21888309, compound

HRID 1167887Notes

Reaction equation

HRID 1167887 reaction equation
C(N(CC)CC)C.[N+:8]([CH2:11][C:12]1([CH2:18][CH2:19][NH2:20])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)([O-:10])=[O:9].[CH3:21][S:22](Cl)(=[O:24])=[O:23]>O1CCCC1>[N+:8]([CH2:11][C:12]1([CH2:18][CH2:19][NH:20][S:22]([CH3:21])(=[O:24])=[O:23])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 12970145HCID 12970145, compound2×

Product 1

HCID 21888309HCID 21888309, compoundYield 47.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (0.64 g, 6.3 mmol) was added dropwise to a mixture of the amine hydrochloride salt (compound 4, 0.70 g, 3.1 mmol) and methane sulfonyl chloride (0.36 g, 6.3 mmol) in tetrahydrofuran (35 mL). After stirring at room temperature for 2 hours, the mixture was filtered, diluted with ethyl acetate, and washed with dilute hydrochloric acid, saturated sodium bicarbonate solution, and water, dried over magnesium sulphate, filtered, and evaporated to dryness. The residue was crystallized from ethyl acetate/heptane to give colorless crystals (0.39 g, 47%); mp 86-88° C.

Workup

  1. filtrationthe mixture was filtered
  2. additiondiluted with ethyl acetate
  3. washwashed with dilute hydrochloric acid, saturated sodium bicarbonate solution, and water
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was crystallized from ethyl acetate/heptane

Sources & evidence

ORD record
ord-9dc30794f4374417817bdd453e23c5e6
Source dataset
uspto-grants-2003_09
Patent number
US06620829B2

Reaction notes

Loading…