Sodium Iodide → N-Methoxy-N-methyl-3-morpholin-4-yl-5-(pentafluorosulfanyl)benzamide

HRID 1258528Notes

Reaction equation

HRID 1258528 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(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+].Br[CH2:29][CH2:30][O:31][CH2:32][CH2:33]Br>CN(C=O)C.CC(=O)OCC>[CH3:10][O:9][N:7]([CH3:8])[C:5](=[O:6])[C:4]1[CH:11]=[C:12]([S:14]([F:19])([F:15])([F:16])([F:17])[F:18])[CH:13]=[C:2]([N:1]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[CH:3]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 21521Bis(2-bromoethyl) etherHCID 580857033-Amino-N-methoxy-N-methyl-5-pentafluorosulfanylbenzamide

Product 1

HCID 58136881N-Methoxy-N-methyl-3-morpholin-4-yl-5-(pentafluorosulfanyl)benzamideYield 32%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

3-Amino-N-methoxy-N-methyl-5-(pentafluorosulfanyl)benzamide (6.3 g, example 4b) was dissolved in DMF (80 ml), and cesium carbonate (10.1 g), sodium iodide (0.62 g) and bis(2-bromoethyl)ether (19.37 g) were added. The mixture was divided between 10 microwave vessels, each of which was heated in the microwave to 130° C. for 3 h. Subsequently, the batches were combined and freed of the solvent. The residue was taken up in EA and washed with water. The EA phase was dried and concentrated. The residue was purified using silica gel (120 g cartridge, n-heptane/EA gradient of 0-100% within 30 min). 2.48 g of the title compound were obtained.

Workup

  1. washwashed with water
  2. dry with materialThe EA phase was dried
  3. concentrationconcentrated
  4. customThe residue was purified
  5. customsilica gel (120 g cartridge, n-heptane/EA gradient of 0-100% within 30 min)

Sources & evidence

ORD record
ord-9e67843018d94d74a82568e889420823
Source dataset
uspto-grants-2013_06
Patent number
US08466169B2

Reaction notes

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