Dimethyl Sulfoxide → HCID 59833360, compound

HRID 269730Notes

Reaction equation

HRID 269730 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:18][C:19]([C:21]2[CH:26]=[CH:25][C:24](F)=[CH:23][N:22]=2)=[O:20])=[C:6]([CH:17]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:11]=1)=[O:8].[CH3:28][S:29](C)=O.C[S-].[Na+]>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:18][C:19]([C:21]2[CH:26]=[CH:25][C:24]([S:29][CH3:28])=[CH:23][N:22]=2)=[O:20])=[C:6]([CH:17]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:11]=1)=[O:8]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 4378561Sodium methanethiolateHCID 21072664HCID 21072664, compound

Product 1

HCID 59833360HCID 59833360, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 5-fluoro-2-[(5-fluoropyridin-2-yl)-carbonylamino]-N-(5-chloropyridin-2-yl)benzamide (502 mg, 1.29 mmol), DMSO (4 mL) and sodium thiomethoxide (95 mg, 1.36 mmoL) was heated to 50° C. for 18 h. The reaction was cooled, added water, filtered, and dried. The solid was triturated with CH2Cl2 and filtered to give the title compound as a white solid (461 mg, 86%).

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. customdried
  4. customThe solid was triturated with CH2Cl2
  5. filtrationfiltered

Sources & evidence

ORD record
ord-a4b8c43945624ac591c4bdf4800e6603
Source dataset
uspto-grants-2008_11
Patent number
US07449457B2

Reaction notes

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