Hydrochloric Acid → HCID 15406907, compound

HRID 1740131Notes

Reaction equation

HRID 1740131 reaction equation
[Br-].[CH:2]1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.CC([O-])(C)C.[K+].[CH:33]([C:35]1[CH:40]=[CH:39][C:38]([C:41]2[C:42]([S:47]([NH2:50])(=[O:49])=[O:48])=[CH:43][CH:44]=[CH:45][CH:46]=2)=[CH:37][CH:36]=1)=O.Cl>C1COCC1.CC(=O)OCC>[C:2]1(=[CH:33][C:35]2[CH:40]=[CH:39][C:38]([C:41]3[C:42]([S:47]([NH2:50])(=[O:49])=[O:48])=[CH:43][CH:44]=[CH:45][CH:46]=3)=[CH:37][CH:36]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 2724861Cyclohexyl(triphenyl)phosphanium bromideHCID 15406906HCID 15406906, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 15406907HCID 15406907, compoundYield 39.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

5.5 g of cyclohexyltriphenylphosphonium bromide and 2.6 g of KOtBu were stirred at RT for 4 h in 200 ml of anhydrous THF. 3.0 g of 4'-formylbiphenyl-2-sulfonamide were added and the mixture was stirred at RT for 18 h. It was then diluted with 200 ml of EA, adjusted to pH=6-7 using aqueous HCl solution and washed 2 times with 100 ml of a saturated aqueous NaCl solution each time. The organic phase was dried over Na2SO4 and the solvent was removed in vacuo. Chromatography on silica gel using DIP yielded 1.5 g of a colorless oil.

Workup

  1. washwashed 2 times with 100 ml of a saturated aqueous NaCl solution each time
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-77a8bc365dc044f4921bc17584032c04
Source dataset
uspto-grants-1999_10
Patent number
US05968978

Reaction notes

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