Dimethylformamide → HCID 86705029, compound

HRID 1053279Notes

Reaction equation

HRID 1053279 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](O)=[O:20])=[C:16]([C:22]3[CH:27]=[CH:26][C:25]([S:28](=[O:31])(=[O:30])[NH2:29])=[CH:24][CH:23]=3)[C:15]=2[N:32]([CH3:34])[CH3:33])=[CH:10][CH:9]=1.[CH3:35][N:36]([CH:38]=O)[CH3:37].[CH2:40]([N:42](CC)CC)C>ClCCl>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[S:18][C:17]([C:19]([N:42]([O:5][CH3:1])[CH3:40])=[O:20])=[C:16]([C:22]3[CH:27]=[CH:26][C:25]([S:28](=[O:31])(=[O:30])[N:29]=[CH:35][N:36]([CH3:38])[CH3:37])=[CH:24][CH:23]=3)[C:15]=2[N:32]([CH3:33])[CH3:34])=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 68286089HCID 68286089, compound2×

Product 1

HCID 86705029HCID 86705029, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Oxalyl chloride (0.58 g, 0.39 ml, 4.57 mmol) was added drop wise to a solution of 5-(4-chlorophenyl)-4-(dimethylamino)-3-(4-sulfamoylphenyl)thiophene-2-carboxylic acid (compound 34f, 1.00 g, 2.28 mmol) in a mixture of dichloromethane (30 ml) and DMF (0.33 g, 0.35 ml, 4.57 mmol) at 0° C. The reaction 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 mixture was then concentrated under reduced pressure. The residue so obtained was dissolved in dry dichloromethane (30 ml) and cooled to 0° C. To the cooled reaction mixture was then added triethylamine (1.38 g, 1.90 ml, 13.68 mmol) followed by the addition of N, O-dimethylhydroxylamine hydrochloride (0.40 g, 4.57 mmol) under stirring. The reaction mixture was then stirred at room temperature for 2 hr. The progress of the reaction was monitored by TLC. The reaction mixture was then diluted with DCM (25 ml) and washed with water (2×25 ml). The combined organic layer was then dried over anhydrous sodium sulphate, and concentrated under reduced pressure to obtain a crude product, which was then purified by column chromatography over silica gel (100-200 mesh) using 1.6% methanol in DCM as an eluent to obtain the title compound (0.8 g, 65.35%).

Workup

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. customThe residue so obtained
  3. temperaturecooled to 0° C
  4. customTo the cooled reaction mixture
  5. stirringunder stirring
  6. stirringThe reaction mixture was then stirred at room temperature for 2 hr
  7. washwashed with water (2×25 ml)
  8. dry with materialThe combined organic layer was then dried over anhydrous sodium sulphate
  9. concentrationconcentrated under reduced pressure
  10. customto obtain a crude product, which
  11. customwas then purified by column chromatography over silica gel (100-200 mesh)

Sources & evidence

ORD record
ord-d47ae1554f7c4ba887f632792a231432
Source dataset
uspto-grants-2016_07
Patent number
US09393247B2

Reaction notes

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