Dimethylformamide → HCID 86705033, compound

HRID 1053303Notes

Reaction equation

HRID 1053303 reaction equation
[C:1](Cl)(=[O:5])C(Cl)=O.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:18][C:17]([C:19]([OH:21])=O)=[C:16]([C:22]3[CH:27]=[CH:26][C:25]([S:28](=[O:31])(=[O:30])[NH2:29])=[C:24]([CH3:32])[CH:23]=3)[C:15]=2[CH3:33])=[CH:10][CH:9]=1.[CH3:34][N:35]([CH:37]=O)[CH3:36].[CH2:39]([N:41](CC)CC)C>ClCCl>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:18][C:17]([C:19]([N:41]([O:5][CH3:1])[CH3:39])=[O:21])=[C:16]([C:22]3[CH:27]=[CH:26][C:25]([S:28](=[O:31])(=[O:30])[N:29]=[CH:34][N:35]([CH3:37])[CH3:36])=[C:24]([CH3:32])[CH:23]=3)[C:15]=2[CH3:33])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 68285893HCID 68285893, compound

Product 1

HCID 86705033HCID 86705033, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Oxalyl chloride (0.47 g, 0.32 ml, 3.7 mmol) was added drop wise to a solution of 5-(4-chlorophenyl)-4-methyl-3-(3-methyl-4-sulfamoylphenyl)thiophene-2-carboxylic acid (41d, 0.52 g, 1.23 mmol) in a mixture of dichloromethane (20 ml) and DMF (0.18 g, 0.19 ml, 2.46 mmol) at 0° C. The mixture was then allowed to warm to room temperature and stirred for 1.5 hr under a nitrogen atmosphere. The progress of the reaction was monitored by TLC. The reaction mixture was then concentrated under reduced pressure. The residue so obtained was then dissolved in dry dichloromethane (20 ml) and cooled to 0° C. To the cooled solution so obtained was then added triethylamine (0.74 g, 1.03 ml, 7.39 mmol), which was then followed by addition of N, O-dimethylhydroxylamine hydrochloride (0.24 g, 2.46 mmol) under stirring. The reaction mixture was then stirred at room temperature for 2 hours. The progress of the reaction was monitored by TLC. The reaction mixture was then diluted with DCM (20 ml) and the mixture so obtained was washed with water (2×10 ml). The organic layer obtained was then dried over anhydrous sodium sulphate, and concentrated under reduced pressure to obtain a crude product. The crude product was then purified by column chromatography over silica gel (100-200 mesh) using 0.8% methanol in DCM as an eluent to obtain the title compound (0.34 g, 53%).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customThe residue so obtained
  3. temperaturecooled to 0° C
  4. customTo the cooled solution so obtained
  5. stirringunder stirring
  6. stirringThe reaction mixture was then stirred at room temperature for 2 hours
  7. customthe mixture so obtained
  8. washwas washed with water (2×10 ml)
  9. customThe organic layer obtained
  10. dry with materialwas then dried over anhydrous sodium sulphate
  11. concentrationconcentrated under reduced pressure
  12. customto obtain a crude product
  13. customThe crude product was then purified by column chromatography over silica gel (100-200 mesh)

Sources & evidence

ORD record
ord-831fdc1c359245bf88f46caf3ce4ed31
Source dataset
uspto-grants-2016_07
Patent number
US09393247B2

Reaction notes

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