Hydrochloric Acid → HCID 21889494, compound

HRID 1937277Notes

Reaction equation

HRID 1937277 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH2:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25](=[O:27])[CH3:26])=[CH:20][CH:19]=2)(=[O:17])=[O:16])(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C1(C)C=CC(S([N:37]=[N+:38]=[N-])(=O)=O)=CC=1.C1CCN2C(=NCCC2)CC1.Cl>ClCCl>[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([C:14]([S:15]([C:18]2[CH:19]=[CH:20][C:21]([O:24][C:25](=[O:27])[CH3:26])=[CH:22][CH:23]=2)(=[O:17])=[O:16])=[N+:37]=[N-:38])(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 13661p-Toluenesulfonyl azideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 22460313HCID 22460313, compound

Product 1

HCID 21889494HCID 21889494, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The bis(4-acetyloxyphenylsulfonyl)methane in Synthesis Example 3, 4.5 g (0.011 mol), was dispersed in 49 g of dichloromethane. To the dispersion was added 2.5 g (0.016 mol) of p-toluenesulfonylazide which had been separately prepared. With stirring at room temperature, 3.0 g (0.015 mol) of 1,8-diazabicyclo[5.4.0]-7-undecene (DBU) was added to the dispersion, and after 5 minutes, 50 g of a 0.2N aqueous hydrochloric acid was added to stop reaction. The organic layer was separated and washed with 50 g of water. The organic layer was concentrated and 8 g of the residue was purified by silica gel column chromatography using dichloromethane as an elute. The thus obtained oily product was combined with 10 g of hexane for crystallization, followed by filtration and vacuum drying. There was obtained 1.5 g (yield 31%) of fine yellow crystals.

Workup

  1. customhad been separately prepared
  2. customreaction
  3. customThe organic layer was separated
  4. washwashed with 50 g of water
  5. concentrationThe organic layer was concentrated
  6. custom8 g of the residue was purified by silica gel column chromatography
  7. customThe thus obtained oily product was combined with 10 g of hexane for crystallization
  8. filtrationfollowed by filtration and vacuum
  9. customdrying

Sources & evidence

ORD record
ord-427527ec8e4643c28dac2b5d5c2d6381
Source dataset
uspto-grants-2002_05
Patent number
US06395446B1

Reaction notes

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