Triethylamine → HCID 178476687, compound

HRID 2119999Notes

Reaction equation

HRID 2119999 reaction equation
[CH3:1][S:2]([C:5]1[CH:23]=[CH:22][C:8]([CH:9]=[C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:12]/[C:11]/2=[N:20]\[OH:21])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[C:24](Br)(=[O:26])[CH3:25].C(N(CC)CC)C>ClCCl>[C:24]([O:21]/[N:20]=[C:11]1/[C:10](=[CH:9][C:8]2[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:23][CH:22]=2)[C:19]2[C:14]([CH2:13][CH2:12]/1)=[CH:15][CH:16]=[CH:17][CH:18]=2)(=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10482Acetyl bromideHCID 154041398HCID 154041398, compound

Product 1

HCID 178476687HCID 178476687, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(E)-1-(4-methanesulfonyl-benzylidene)-3,4-dihydro-1H-naphthalene-2-one oxime (25 mg, 0.076 mmol) and acetylbromide (0.017 ml, 0.23 mmol) were added into dichloromethane (2.0 ml). Then, at room temperature triethylamine (0.032 ml, 0.23 mmol) was added, stirred for an hour so as to complete the reaction. Afterward, an organic layer was separated by blending water, washed again with water and saturated brine, and then dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure and made to crystal by using a mixed organic solvent (diethylether/isopropanol/n-hexane=1/1/5, v/v/v). As a result, 16.9 mg of the present compound (productive yield 60%) was obtained as a white solid crystal.

Workup

  1. customthe reaction
  2. customAfterward, an organic layer was separated
  3. washwashed again with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe resulting solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-281f3af1ec4742d3a3dfb4dcc60f9dfa
Source dataset
uspto-grants-2004_02
Patent number
US06686493B2

Reaction notes

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