Triethylamine → HCID 131722890, compound

HRID 1358647Notes

Reaction equation

HRID 1358647 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14]CC(S(N)(=O)=O)C)=[CH:8][CH:7]=2)=[CH:2]1.C([N:24]([CH2:27]C)CC)C.[CH3:29][N:30](C)[S:31](Cl)(=[O:33])=[O:32]>ClCCl>[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[CH:8][C:9]([CH2:12][CH2:13][CH2:14][N:24]([CH3:27])[S:31]([NH:30][CH3:29])(=[O:33])=[O:32])=[CH:10][CH:11]=2)=[CH:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 83372Dimethylsulphamoyl chlorideHCID 86584131HCID 86584131, compound

Product 1

HCID 131722890HCID 131722890, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.5 g (1.5 mmol) of material from Example 28, Step B and 0.52 mL (3.70 mmol) of triethylamine in 10 mL of dichloromethane was cooled to 0° C. A solution of 0.16 mL (1.5 mmol) of dimethylsulfamoyl chloride in 1 mL of dichloro-methane was added dropwise. The ice-bath was removed and the mixture was stirred at ambient temperature for 5 h. The mixture was washed with 10 mL of 10% aqueous sodium bisulfate, the organic layer was separated and the aqueous layer extracted three times with 5 mL of dichloromethane. The combined organics were dried (MgSO4), filtered and concentrated in vacuo. The residue was suspended in 50% ether/hexane and filtered to afford 0.22 g (46%) of the title compound.

Workup

  1. customThe ice-bath was removed
  2. washThe mixture was washed with 10 mL of 10% aqueous sodium bisulfate
  3. customthe organic layer was separated
  4. extractionthe aqueous layer extracted three times with 5 mL of dichloromethane
  5. dry with materialThe combined organics were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. filtrationfiltered

Sources & evidence

ORD record
ord-d1de831646b0448fa9b50515b2d60423
Source dataset
uspto-grants-2003_07
Patent number
US06596716B2

Reaction notes

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