Triethylamine → HCID 86758908, compound

HRID 1264536Notes

Reaction equation

HRID 1264536 reaction equation
[C:1]1([CH2:11][N:12]([C:16]2[O:20][N:19]=[C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:17]=2)[CH2:13][CH2:14][OH:15])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>C(Cl)Cl>[C:1]1([CH2:11][N:12]([C:16]2[O:20][N:19]=[C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:17]=2)[CH2:13][CH2:14][O:15][S:35]([CH3:34])(=[O:37])=[O:36])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18612673HCID 18612673, compound

Product 1

HCID 86758908HCID 86758908, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[Naphthalen-1-ylmethyl-(3-phenylisoxazol-5-yl)amino]ethanol (820 mg, 2.38 mmol) was dissolved in methylene chloride (15 ml), treated with triethylamine (592 μl, 4.25 mmol) followed by methanesulfonyl-chloride (265 μl, 3.42 mnmol) and the solution stirred at rt for 1.5 hr. The reaction was washed with 50% sodium bicarbonate (aq, 2×), water (1×), and brine (1×), dried over sodium sulfate, filtered and stripped to dryness in vacuo to give the product as a sticky, foam (1.07 gm, quantitative).

Workup

  1. washThe reaction was washed with 50% sodium bicarbonate (aq, 2×), water (1×), and brine (1×)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customto give the product as a sticky, foam (1.07 gm, quantitative)

Sources & evidence

ORD record
ord-9fe3578b4b5c4ac4a2d31bfc48cce785
Source dataset
uspto-grants-2003_04
Patent number
US06544982B1

Reaction notes

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