Acetic Anhydride → 3-Acetylamino-N-methoxy-N-methyl-5-(pentafluorosulfanyl)benzamide

HRID 658017Notes

Reaction equation

HRID 658017 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:11]=[C:12]([S:14]([F:19])([F:18])([F:17])([F:16])[F:15])[CH:13]=1)[C:5]([N:7]([O:9][CH3:10])[CH3:8])=[O:6].C(N(CC)CC)C.[C:27](OC(=O)C)(=[O:29])[CH3:28].C(=O)([O-])O.[Na+]>C(Cl)Cl.O>[C:27]([NH:1][C:2]1[CH:3]=[C:4]([CH:11]=[C:12]([S:14]([F:19])([F:15])([F:16])([F:17])[F:18])[CH:13]=1)[C:5]([N:7]([O:9][CH3:10])[CH3:8])=[O:6])(=[O:29])[CH3:28]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 580857033-Amino-N-methoxy-N-methyl-5-pentafluorosulfanylbenzamide

Product 1

HCID 581368203-Acetylamino-N-methoxy-N-methyl-5-(pentafluorosulfanyl)benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

3-Amino-N-methoxy-N-methyl-5-pentafluorosulfanylbenzamide (1.2 g) was dissolved in methylene chloride (15 ml), and triethylamine (0.7 ml) followed by acetic anhydride (1.75 ml) were added while stirring with exclusion of moisture. After stirring at RT for 3 h, water and saturated sodium hydrogencarbonate solution were added, the phases were separated and the methylene chloride phase was washed three times more with water, dried over magnesium sulfate, filtered and concentrated. The resulting product (1.3 g) was used in the next stage without further purification.

Workup

  1. additionwere added
  2. stirringAfter stirring at RT for 3 h
  3. customthe phases were separated
  4. washthe methylene chloride phase was washed three times more with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting product (1.3 g) was used in the next stage without further purification

Sources & evidence

ORD record
ord-b8953681347e4e02985784127a304c7f
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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