Dimethylformamide → HCID 19811584, compound

HRID 373103Notes

Reaction equation

HRID 373103 reaction equation
O=S(Cl)[Cl:3].[CH2:5]([C:7]([CH2:18][C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)([CH2:16][CH3:17])[CH:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)O)[CH3:6].CN(C)C=O.[OH-].[Na+]>C1(C)C=CC=CC=1>[Cl:3][CH:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:7]([CH2:16][CH3:17])([CH2:18][C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)[CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 19811583HCID 19811583, compound

Product 1

HCID 19811584HCID 19811584, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

13.3 g (0.11 mol) of SOCl2 are added dropwise, at 80° C., to 5 g (0.018 mol) of 2-ethyl-1-phenyl-2-(pyrid-3-ylmethyl)-butanol in 100 ml of toluene and a catalytic amount (0.1 g) of dimethylformamide, and the mixture is left for 5 hours at this temperature. The mixture is cooled, poured onto ice water and then rendered alkaline with 30% strength NaOH solution. The aqueous phase is extracted with three times 50 ml of tert-butyl methyl ether and the combined organic phases are dried over MgSO4. After the solvent has been evaporated off, the residue is chromatographed over silica gel (1 : 1 toluene/ethyl acetate). 2.07 g (yield 40%) of the title compound are obtained as a viscous yellow oil (compound No. 581).

Workup

  1. temperatureThe mixture is cooled
  2. additionpoured onto ice water
  3. extractionThe aqueous phase is extracted with three times 50 ml of tert-butyl methyl ether
  4. dry with materialthe combined organic phases are dried over MgSO4
  5. customAfter the solvent has been evaporated off
  6. customthe residue is chromatographed over silica gel (1 : 1 toluene/ethyl acetate)

Sources & evidence

ORD record
ord-0f56212a73444670be9f7568e67170f1
Source dataset
uspto-grants-1992_11
Patent number
US05162329

Reaction notes

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