Triethylamine → HCID 13851113, compound

HRID 543294Notes

Reaction equation

HRID 543294 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:22]=[C:21]2[C:16]([CH:17]=[CH:18][C:19]([NH2:23])=[CH:20]2)=[CH:15][CH:14]=1.C(N(CC)CC)C.[CH2:31]([S:33](Cl)(=[O:35])=[O:34])[CH3:32]>O1CCCC1>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:22]=[C:21]2[C:16]([CH:17]=[CH:18][C:19]([NH:23][S:33]([CH2:31][CH3:32])(=[O:35])=[O:34])=[CH:20]2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 13851112HCID 13851112, compound

Product 1

HCID 13851113HCID 13851113, compoundYield 74.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5.00 g 7-(2-quinolinylmethoxy)-2-naphthalenamine (17 mmol), prepared according to the procedure of Example 7, 1.7 g triethylamine (17 mmol) and 2.18 g ethanesulfonyl chloride (17 mmol) in 50 mL tetrahydrofuran is refluxed overnight. The solvent is removed and the residue is partitioned between methylene chloride and saturated sodium bicarbonate. After drying over potassium carbonate, the organic layer is freed of solvent to afford 5.00 g of a brown gum. Chromatography on alumina and elution with 9:1 methylene chloride/ethyl acetate affords 1.4 g of a white solid which is recrystallized from ethyl acetate. Rechromatography on HPLC and final recrystallization from ethyl acetate affords 0.6 g (9%) of white crystals, m.p. 166°-167.5° C.

Workup

  1. temperatureis refluxed overnight
  2. customThe solvent is removed
  3. customthe residue is partitioned between methylene chloride and saturated sodium bicarbonate
  4. dry with materialAfter drying over potassium carbonate

Sources & evidence

ORD record
ord-0ab66915949540b7a3e30abcf796e5ea
Source dataset
uspto-grants-1987_04
Patent number
US04661596

Reaction notes

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