Sodium Chloride → HCID 53997388, compound

HRID 6202Notes

Reaction equation

HRID 6202 reaction equation
C([O:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]([C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1)[CH2:10][CH2:11][CH2:12][CH3:13])(=O)C.[Br-].[O:23]1CCO[CH:24]1[CH2:28][P+](CCCC)(CCCC)CCCC.CC(C)([O-])C.[K+].[Cl-].[Na+]>CN(C)C=O.Cl.O>[OH:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]([C:14]1[CH:15]=[CH:16][C:17]([CH:18]=[CH:28][CH:24]=[O:23])=[CH:20][CH:21]=1)[CH2:10][CH2:11][CH2:12][CH3:13]

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 110117524-(N-4-acetoxybutyl-N-butylamino)benzaldehydeHCID 22292430Tributyl(1,3-dioxolan-2-ylmethyl)phosphonium BromideHCID 23665647Potassium tert-butoxide

Product 1

HCID 53997388HCID 53997388, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
90 °C

Procedure

To a solution of 29.1 g (0.1 mole) of 4-(N-4-acetoxybutyl-N-butylamino)benzaldehyde in dimethylformamide is added 73.9 g (0.2 mole) of 1,3-dioxolan-2-ylmethyltributylphosphonium bromide in dimethylformamide, and the mixture is heated at 90° C. Potassium t-butoxide (22.4 g, 0.2 mole) is added, and heating is continued at 90° C. for 16 hours. After cooling to room temperature, the product solution is poured into a seven-fold excess of water, the aqueous mixture is saturated with sodium chloride and the solution is extracted with three portions of ether. The combined organics are dried over 4A sieves, filtered through cotton, and evaporated. The crude reaction product is then dissolved in 3M HCl, and the reaction is stirred at room temperature for 16 hours. After neutralization with saturated sodium bicarbonate, the aqueous mixture is extracted with three portions of ether, and the combined organics are passed through silica gel, dried over 4A sieves, filtered through cotton, and evaporated to yield compound A. The product is purified by flash chromatography (silica gel, 1:1 hexane:ethyl acetate).

Workup

  1. temperatureheating
  2. temperatureAfter cooling to room temperature
  3. extractionthe solution is extracted with three portions of ether
  4. dry with materialThe combined organics are dried over 4A sieves
  5. filtrationfiltered through cotton
  6. customevaporated
  7. customThe crude reaction product
  8. extractionAfter neutralization with saturated sodium bicarbonate, the aqueous mixture is extracted with three portions of ether
  9. dry with materialdried over 4A sieves
  10. filtrationfiltered through cotton
  11. customevaporated

Sources & evidence

ORD record
ord-a8052ae73acf41bcbeb0aa54d437ed4a
Source dataset
uspto-grants-1993_09
Patent number
US05247042

Reaction notes

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