Triethylamine → HCID 86705022, compound

HRID 1518680Notes

Reaction equation

HRID 1518680 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)[C:15]=2[CH3:32])=[CH:10][CH:9]=1.[CH2:33]([N:35]([CH2:38]C)[CH2:36]C)C.Cl.[CH3:41][NH:42][O:43][CH3:44]>ClCCl.CN(C=O)C>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[S:18][C:17]([C:19]([N:42]([O:43][CH3:44])[CH3:41])=[O:20])=[C:16]([C:22]3[CH:27]=[CH:26][C:25]([S:28](=[O:31])(=[O:30])[N:29]=[CH:33][N:35]([CH3:38])[CH3:36])=[CH:24][CH:23]=3)[C:15]=2[CH3:32])=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 68285720HCID 68285720, compound2×

Product 1

HCID 86705022HCID 86705022, compoundYield 86.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride (2.1 g, 1.4 ml, 16.2 mmol) was added dropwise at 0° C. to a solution of 5-(4-chlorophenyl)-4-methyl-3-(4-sulfamoylphenyl)thiophene-2-carboxylic acid (compound 1c, 2.2 g, 5.4 mmol) in a mixture of dichloromethane (40 ml) and DMF (0.8 g, 0.8 ml, 10.8 m mol). The resulting mixture was allowed to warm to room temperature and stirred for 1.5 hr, under a nitrogen atmosphere. The progress of reaction was monitored by TLC. The reaction mixture was concentrated under reduced pressure and used directly for further reaction. The residue so obtained was dissolved in dry dichloromethane (40 ml) and to this was added triethylamine (2.8 g, 3.9 ml, 27.0 mmol) followed by the addition of N,O-dimethylhydroxylamine hydrochloride (1.06 g, 10.8 mmol) under stirring. The reaction mixture was stirred at room temperature for 2 hr. The progress of reaction was monitored by TLC. The reaction mixture was washed with water (2×20 ml) and the organic layer obtained was dried over anhydrous sodium sulphate, and concentrated under reduced pressure to obtain a crude product. The crude product was further purified by column chromatography over silica gel (100-200 mesh) using 80% ethylacetate in hexane as an eluent to obtain the title compound (2.36 g, 86%).

Workup

  1. customThe progress of reaction
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customused directly for further reaction
  4. customThe residue so obtained
  5. stirringunder stirring
  6. stirringThe reaction mixture was stirred at room temperature for 2 hr
  7. customThe progress of reaction
  8. washThe reaction mixture was washed with water (2×20 ml)
  9. customthe organic layer obtained
  10. dry with materialwas dried over anhydrous sodium sulphate
  11. concentrationconcentrated under reduced pressure
  12. customto obtain a crude product
  13. customThe crude product was further purified by column chromatography over silica gel (100-200 mesh)

Sources & evidence

ORD record
ord-9ad7c886147e4048b74b550e3938c324
Source dataset
uspto-grants-2015_07
Patent number
US09072731B2

Reaction notes

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