Hydrochloric Acid → HCID 22460302, compound

HRID 1937278Notes

Reaction equation

HRID 1937278 reaction equation
[C:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([CH2:19][S:20]([C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30](=[O:37])[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:25][CH:24]=2)(=[O:22])=[O:21])(=[O:18])=[O:17])=[CH:12][CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S([N:47]=[N+:48]=[N-])(=O)=O)=CC=1.C1CCN2C(=NCCC2)CC1.Cl>ClCCl>[C:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([C:19]([S:20]([C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30](=[O:37])[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:25][CH:24]=2)(=[O:22])=[O:21])=[N+:47]=[N-:48])(=[O:17])=[O:18])=[CH:12][CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 13661p-Toluenesulfonyl azideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 22460305HCID 22460305, compound

Product 1

HCID 22460302HCID 22460302, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The bis(4-benzoyloxyphenylsulfonyl)methane in Synthesis Example 6, 10 g (0.019 mol), was dispersed in 200 g of dichloromethane. To the dispersion was added 5.6 g (0.029 mol) of p-toluenesulfonylazide which had been separately prepared. With stirring under ice cooling, 4.0 g (0.026 mol) of DBU was added to the dispersion, and after 5 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 15 g of the residue was purified by silica gel column chromatography using dichloromethane as an elute. The thus obtained oily product was combined with 40 g of hexane for crystallization, followed by filtration and vacuum drying. There was obtained 4.0 g (yield 37%) of fine yellow crystals.

Workup

  1. customhad been separately prepared
  2. customreaction
  3. customThe organic layer was separated
  4. washwashed with 100 g of water
  5. concentrationThe organic layer was concentrated
  6. custom15 g of the residue was purified by silica gel column chromatography
  7. customThe thus obtained oily product was combined with 40 g of hexane for crystallization
  8. filtrationfollowed by filtration and vacuum
  9. customdrying

Sources & evidence

ORD record
ord-80c867188f3447ac92eb92bf1eba9e3f
Source dataset
uspto-grants-2002_05
Patent number
US06395446B1

Reaction notes

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