Acetyl chloride → HCID 58137450, compound

HRID 1258510Notes

Reaction equation

HRID 1258510 reaction equation
[NH2:1][C:2]1[C:3]([S:15]([F:20])([F:19])([F:18])([F:17])[F:16])=[CH:4][C:5]([CH3:14])=[C:6]([CH:13]=1)[C:7]([N:9]([O:11][CH3:12])[CH3:10])=[O:8].C(N(CC)CC)C.[C:28](Cl)(=[O:30])[CH3:29].C(=O)([O-])O.[Na+]>ClCCl.O>[C:28]([NH:1][C:2]1[C:3]([S:15]([F:20])([F:16])([F:17])([F:18])[F:19])=[CH:4][C:5]([CH3:14])=[C:6]([CH:13]=1)[C:7]([N:9]([O:11][CH3:12])[CH3:10])=[O:8])(=[O:30])[CH3:29]

Participants

7

Reactant 4

HCID 6367Acetyl chloride2×HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 58137436HCID 58137436, compound

Product 1

HCID 58137450HCID 58137450, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

5-Amino-N-methoxy-2,N-dimethyl-4-(pentafluorosulfanyl)benzamide (200 mg) was dissolved in dichloromethane (10 ml) and then triethylamine (100 μl) and acetyl chloride (50 μl) were added while stirring. After 2 h, further acetyl chloride was added (50 μl) and the mixture was stirred for 4 h. Then the reaction mixture was admixed with water and saturated sodium hydrogencarbonate solution, and the organic phase was removed and washed three times with water. After drying over magnesium sulfate, the organic phase was filtered and concentrated. The residue was purified by means of preparative HPLC. The product-containing fractions were combined, freed of the acetonitrile, admixed with saturated sodium hydrogencarbonate solution and extracted three times with ethyl acetate. The combined extracts were dried over magnesium sulfate, filtered and concentrated. 170 mg of the desired compound were obtained.

Workup

  1. stirringthe mixture was stirred for 4 h
  2. customthe organic phase was removed
  3. washwashed three times with water
  4. dry with materialAfter drying over magnesium sulfate
  5. filtrationthe organic phase was filtered
  6. concentrationconcentrated
  7. customThe residue was purified by means of preparative HPLC
  8. extractionextracted three times with ethyl acetate
  9. dry with materialThe combined extracts were dried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-9e48102521a14475bf861f361778e925
Source dataset
uspto-grants-2013_06
Patent number
US08466169B2

Reaction notes

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