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

HRID 532390
Notes
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Reaction equation

HRID 532390 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 6228DimethylformamideSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

3-Amino-N-methoxy-N-methyl-5-(pentafluorosulfanyl)benzamide (O5.075; 6.3 g) 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 to 130° C. for 3 h. Subsequently, the batches were combined and freed of 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-b0eb5626dc754def928e1e88ac969627
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08853206B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes