Triethylamine → HCID 21888309, compound

HRID 722835Notes

Reaction equation

HRID 722835 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-744e336a09c943549f7af868dfd799f4
Source dataset
uspto-grants-2006_11
Patent number
US07138542B2

Reaction notes

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