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

HRID 1524580Notes

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

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. LC-MS rt: 1.41 min [M+H]+: 377.0 (met. a)

Workup

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

Sources & evidence

ORD record: ord-186dc8882f104543b2f2ba872beda8b7
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079906B2

Reaction notes

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