Thionyl Chloride → 3-Dimethylamino-N-methoxy-N-methyl-5-pentafluorosulfanylbenzamide

HRID 249712Notes

Reaction equation

HRID 249712 reaction equation
[CH3:1][N:2]([CH3:18])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([S:12]([F:17])([F:16])([F:15])([F:14])[F:13])[CH:11]=1)[C:6](O)=[O:7].S(Cl)(Cl)=O.Cl.[CH3:24][NH:25][O:26][CH3:27].CCN(C(C)C)C(C)C>C(Cl)Cl.C(OCC)(=O)C>[CH3:1][N:2]([CH3:18])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([S:12]([F:14])([F:17])([F:16])([F:13])[F:15])[CH:11]=1)[C:6]([N:25]([O:26][CH3:27])[CH3:24])=[O:7]

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 580857113-Dimethylamino-5-pentafluorosulfanylbenzoic acid

Product 1

HCID 580857043-Dimethylamino-N-methoxy-N-methyl-5-pentafluorosulfanylbenzamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

3-Dimethylamino-5-pentafluorosulfanylbenzoic acid (1.0 g) was dissolved in methylene chloride (60 ml). Thionyl chloride (5 ml) was added with stirring and the mixture was stirred at RT for 2 h. To complete the reaction, it was subsequently heated at reflux for 3 h. After cooling, the solvent was stripped off, and the residue was dissolved in methylene chloride (50 ml), treated with N,O-dimethylhydroxylamine hydrochloride and Hünig's base (1 ml) was added. After stirring for one hour, the solvent was stripped off, and the residue was taken up with ethyl acetate and washed 5 times with water. The organic phase was dried with magnesium sulfate, filtered and concentrated. 980 mg of the title compound were obtained, which were reacted directly in the next stage.

Workup

  1. stirringthe mixture was stirred at RT for 2 h
  2. customthe reaction, it
  3. temperaturewas subsequently heated
  4. temperatureat reflux for 3 h
  5. temperatureAfter cooling
  6. additionwas added
  7. stirringAfter stirring for one hour
  8. washwashed 5 times with water
  9. dry with materialThe organic phase was dried with magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-6dc0db447ea64bc3b2e3897028d84467
Source dataset
uspto-grants-2011_01
Patent number
US07863269B2

Reaction notes

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