Benzoyl chloride → HCID 24899463, compound

HRID 602722Notes

Reaction equation

HRID 602722 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=3)=[CH:11][C:10]([CH2:23][CH2:24][NH2:25])=[C:9]2[CH3:26])=[CH:4][CH:3]=1.[C:27](Cl)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:20])=[O:21])=[CH:15][CH:14]=3)=[CH:11][C:10]([CH2:23][CH2:24][NH:25][C:27](=[O:34])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[C:9]2[CH3:26])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 24899464HCID 24899464, compound

Product 1

HCID 24899463HCID 24899463, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(1-(4-fluorophenyl)-2-methyl-5-(4-(methylsulphonyl)phenyl)-1H-pyrrol-3-yl)ethanamine (0.20 mmol) in dry DMF (10 mL) cooled at 0° C. and under an atmosphere of N2, TEA (0.20 mmol) was added and the mixture was stirred for 10 min. Then benzoyl chloride (0.20 mmol) was added at 0° C., and the reaction was stirred for 24 h at r.t.; the reaction mixture was washed with water, dried over Na2SO4 and evaporated to dryness in vacuo. The residue, purified by flash-chromatography (EtOAc/hexane 7:3 v/v), gave the expected compound as yellow oil (yield 70%). 1H-NMR (CDCl3) δ ppm: 2.03 (s, 3H), 2.80 (t, 2H, J=7.1), 2.97 (s, 3H), 3.67 (m, 2H), 6.43-6.48 (m, 2H), 7.10 (m, 6H), 7.34-7.46 (m, 3H), 7.64 (m, 2H), 7.75 (m, 2H).

Workup

  1. stirringthe reaction was stirred for 24 h at r.t.
  2. washthe reaction mixture was washed with water
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness in vacuo
  5. customThe residue, purified by flash-chromatography (EtOAc/hexane 7:3 v/v)

Sources & evidence

ORD record
ord-e9763986ff324a93a6c6c810cd50effd
Source dataset
uspto-grants-2011_03
Patent number
US07906551B2

Reaction notes

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