Hexane → HCID 8721397, compound

HRID 1772851Notes

Reaction equation

HRID 1772851 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=1)(=[O:10])=[O:9].Cl[C:23](Cl)([O:25]C(=O)OC(Cl)(Cl)Cl)Cl.CCCCCC.CCOC(C)=O>O1CCOCC1>[CH3:21][O:20][C:14]1[CH:13]=[C:12]([N:11]2[C:23](=[O:25])[NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[S:8]2(=[O:10])=[O:9])[CH:17]=[CH:16][C:15]=1[O:18][CH3:19]

Participants

6

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 94429TriphosgeneHCID 28552743HCID 28552743, compound

Product 1

HCID 8721397HCID 8721397, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-amino-N-(3,4-dimethoxyphenyl)benzenesulfonamide (0.8 g, 2.6 mmol) and triphosgene (0.99 g, 3.4 mmol) in anhydrous 1,4-dioxane was heated in a sealed tube at 100° C. overnight with TLC monitoring (hexane:EtOAc, 1:1). After concentration in vacuo H2O (30 mL) was added and the mixture was extracted with EtOAc (3×100 mL). The combined organic layer was dried over Na2SO4, filtered and concentrated in vacuo. Purification by gradient flash chromatography, eluting with 20-25% EtOAc in hexane yielded the title compound (0.4 g, 1.20 mmol).

Workup

  1. concentrationAfter concentration in vacuo H2O (30 mL)
  2. additionwas added
  3. extractionthe mixture was extracted with EtOAc (3×100 mL)
  4. dry with materialThe combined organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by gradient flash chromatography
  8. washeluting with 20-25% EtOAc in hexane

Sources & evidence

ORD record
ord-b4fc451c1c2e448a8ce4fec04d99bac8
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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