Benzoyl chloride → HCID 68423159, compound

HRID 509206Notes

Reaction equation

HRID 509206 reaction equation
[C:1]1([CH:7]([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[C:8]([O:10][CH3:11])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CC#N.C(OCC)(=O)C>[C:25]([N:15]1[CH2:16][CH2:17][CH:12]([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]([O:10][CH3:11])=[O:9])[CH2:13][CH2:14]1)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 57779708HCID 57779708, compound

Product 1

HCID 68423159HCID 68423159, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirring solution of compound 92 (0.159 g, 0.682 mmol) and triethylamine (0.2 mL, 1.435 mmol) in MeCN (10 mL) was added benzoyl chloride (0.10 mL, 0.862 mmol) and the reaction mixture was stirred for 2 h at room temperature. The reaction was diluted with ethyl acetate, washed with sat. aq. Na2CO3, water, brine, dried over Na2SO4, filtered and concentrated to afford the desired compound (0.196 g, 85%) as a colorless oil. LRMS (ESI): (calc) 337.41 (found) 338.35 (MH)+

Workup

  1. washwashed with sat. aq. Na2CO3, water, brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e991c5285be64de48fd596ab03f180b1
Source dataset
uspto-grants-2015_08
Patent number
US09096565B2

Reaction notes

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