Dimethylformamide → HCID 86705028, compound

HRID 1518703Notes

Reaction equation

HRID 1518703 reaction equation
C(Cl)(=O)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)[CH:15]=2)=[CH:10][CH:9]=1.[CH3:32][N:33]([CH:35]=O)[CH3:34].C(N(CC)CC)C.Cl.[CH3:45][NH:46][O:47][CH3:48]>ClCCl>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:18][C:17]([C:19]([N:46]([O:47][CH3:48])[CH3:45])=[O:20])=[C:16]([C:22]3[CH:23]=[CH:24][C:25]([S:28](=[O:31])(=[O:30])[N:29]=[CH:35][N:33]([CH3:32])[CH3:34])=[CH:26][CH:27]=3)[CH:15]=2)=[CH:10][CH:9]=1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 68285339HCID 68285339, compound2×

Product 1

HCID 86705028HCID 86705028, compoundYield 65.69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Oxalyl chloride (0.70 g, 0.48 ml, 5.58 mmol) was added drop wise at 0° C. to a solution of 5-(4-chlorophenyl)-3-(4-sulfamoylphenyl)thiophene-2-carboxylic acid (compound 33c, 1.10 g, 2.79 mmol) in a mixture of dichloromethane (30 ml) and DMF (0.40 g, 0.43 ml, 5.58 mmol). 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 dissolved in dry dichloromethane (30 ml) and the mixture was then cooled to 0° C. To the cooled mixture was added triethylamine (1.69 g, 2.32 ml, 16.75 mmol) followed by the addition of N,O-dimethylhydroxylamine hydrochloride (0.54 g, 5.58 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) and organic layer so obtained was dried over anhydrous sodium sulphate, and concentrated under reduced pressure to obtain a crude product. The crude product was then purified by flash column chromatography using 0.8% methanol in DCM as an eluent to obtain the title compound (0.9 g, 65.69%).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customThe residue so obtained
  3. temperaturethe mixture was then cooled to 0° C
  4. stirringunder stirring
  5. stirringThe reaction mixture was then stirred at room temperature for 2 hr
  6. washwashed with water (2×25 ml) and organic layer
  7. customso obtained
  8. dry with materialwas dried over anhydrous sodium sulphate
  9. concentrationconcentrated under reduced pressure
  10. customto obtain a crude product
  11. customThe crude product was then purified by flash column chromatography

Sources & evidence

ORD record
ord-a083a12e44c94e3dbb0ec88218383b0a
Source dataset
uspto-grants-2015_07
Patent number
US09072731B2

Reaction notes

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