Hydrochloric Acid → HCID 13006802, compound

HRID 1250427Notes

Reaction equation

HRID 1250427 reaction equation
[CH:1]1([S:7]([CH2:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][S:21]([CH3:24])(=[O:23])=[O:22])=[CH:16][CH:15]=2)(=[O:13])=[O:12])(=[O:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1(C)C=CC(S([N:34]=[N+:35]=[N-])(=O)=O)=CC=1.C1CCN2C(=NCCC2)CC1.Cl>ClCCl>[CH:1]1([S:7]([C:10]([S:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][S:21]([CH3:24])(=[O:22])=[O:23])=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[N+:34]=[N-:35])(=[O:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 13661p-Toluenesulfonyl azideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 13006801HCID 13006801, compound

Product 1

HCID 13006802HCID 13006802, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The cyclohexylsulfonyl(4-methanesulfonyloxyphenylsulfonyl)methane in Synthesis Example 12, 10 g (0.025 mol), was dispersed in 150 g of dichloromethane. To the dispersion was added 4.6 g (0.03 mol) of p-toluenesulfonylazide. With stirring under ice cooling, 4.9 g (0.025 mol) of DBU was added to the dispersion, and after 10 minutes, 100 g of a 0.2N aqueous hydrochloric acid was added to stop reaction. The organic layer was separated and washed with 100 g of water. The organic layer was concentrated and 13 g of the residue was purified by silica gel column chromatography using dichloromethane as an elute. The thus obtained oily product was combined with 20 g of hexane for crystallization, followed by filtration and vacuum drying. There was obtained 4.0 g (yield 38%) of fine yellow crystals.

Workup

  1. customreaction
  2. customThe organic layer was separated
  3. washwashed with 100 g of water
  4. concentrationThe organic layer was concentrated
  5. custom13 g of the residue was purified by silica gel column chromatography
  6. customThe thus obtained oily product was combined with 20 g of hexane for crystallization
  7. filtrationfollowed by filtration and vacuum
  8. customdrying

Sources & evidence

ORD record
ord-155646f3d8a440c3a015afa3b8e08423
Source dataset
uspto-grants-2002_01
Patent number
US06338931B1

Reaction notes

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