Chloroform → HCID 86695312, compound

HRID 2369447Notes

Reaction equation

HRID 2369447 reaction equation
[Br:1][C:2]1[CH:15]=[C:14]2[C:5]([S:6][C:7]3[CH:8]=[CH:9][C:10]([NH:17][C:18](=[O:20])[CH3:19])=[CH:11][C:12]=3[C:13]2=[O:16])=[CH:4][CH:3]=1.[H-].[Na+].CI.[CH:25](Cl)(Cl)Cl>C1COCC1>[Br:1][C:2]1[CH:15]=[C:14]2[C:5]([S:6][C:7]3[CH:8]=[CH:9][C:10]([N:17]([CH3:25])[C:18](=[O:20])[CH3:19])=[CH:11][C:12]=3[C:13]2=[O:16])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86695313HCID 86695313, compound

Product 1

HCID 86695312HCID 86695312, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1.1 g (3.2 mmol) acetamide 23 in 20 mL of THF was added 0.17 g (4.2 mmol) of NaH (60%) under N2. The mixture was stirred for 15 min followed by the dropwise addition of 0.70 g (4.9 mmol) of methyl iodide. The reaction mixture was stirred at room temperature for 48 h and then concentrated in vacuo to obtain a solid residue. To the residue was added CHCl3, followed by filtration and concentration of the filtrate in vacuo to obtain 1.1 g (97% yield) of methyl amide (25) as a yellow solid, mp 240-241° C. 1H-NMR (400 MHz, CDCl3): 1.93 (3H, s), 3.34 (3H, s), 7.46-7.54 (2H, m), 7.66 (1H, d, J=8.7 Hz), 7.76 (1H, d, J=8.7 Hz), 8.45 (1H, s), 8.75 (1H, s).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 48 h
  2. concentrationconcentrated in vacuo
  3. customto obtain a solid residue
  4. filtrationfollowed by filtration and concentration of the filtrate in vacuo

Sources & evidence

ORD record
ord-87d394968d964d588e582bf4346622e6
Source dataset
uspto-grants-2014_04
Patent number
US08703970B2

Reaction notes

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