Dimethyl Sulfoxide → HCID 19761001, compound

HRID 249277Notes

Reaction equation

HRID 249277 reaction equation
CS(C)=[O:3].C(Cl)(=O)[C:6](Cl)=[O:7].[CH2:11]([N:13]([CH2:37][CH3:38])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH:27]([OH:36])[CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:23][CH:22]=1)[CH3:12].C(N(CC)CC)C.[CH2:46]([Cl:48])[Cl:47]>O>[OH-:3].[NH4+:13].[CH3:6][OH:7].[CH2:46]([Cl:48])[Cl:47].[CH2:37]([N:13]([CH2:11][CH3:12])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][C:21]1[CH:22]=[CH:23][C:24]([C:27](=[O:36])[CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:25][CH:26]=1)[CH3:38]

Participants

8

Reactant 5

HCID 679Dimethyl SulfoxideHCID 6344Dichloromethane3×HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 19761004HCID 19761004, compound

Product 2

HCID 19761001HCID 19761001, compoundYield 37%HCID 21896990Dichloromethane methanol ammonium hydroxide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1.58 ml of dimethyl sulphoxide in 10 ml of methylene chloride was added dropwise at -60° during 5 minutes to a solution of 0.8 ml of oxalyl chloride in 30 ml of methylene chloride. After stirring for 2 minutes a solution of the crude 1-[4-[[6-(diethylamino)hexyl]oxy]phenyl]-3-phenylpropanol in 20 ml of methylene chloride was added thereto at -60° within 10 minutes. After 15 minutes 7.5 ml of triethylamine were added thereto at -60° and the reaction mixture was left to warm to room temperature. After one hour at room temperature 100 ml of water were added thereto, the organic phase was separated and the aqueous phase was extracted twice with 100 ml of methylene chloride each time. The combined organic phases were dried over magnesium sulphate and evaporated. After chromatogrpahy of the residue on 240 g of silica gel with ammonium hydroxide/methanol/methylene chloride (1:10:90 ) there were obtained 1.76 g (37%) of 4'-[[6-(diethylamino)hexyl]oxy]-3-phenylpropiophenone as a yellow oil which crystallizes upon standing; m.p. 83°-84°.

Workup

  1. additionwas added
  2. waitat -60° and the reaction mixture was left
  3. customthe organic phase was separated
  4. extractionthe aqueous phase was extracted twice with 100 ml of methylene chloride each time
  5. dry with materialThe combined organic phases were dried over magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-5f81fdc55e45491084c2a0ffe14cfa53
Source dataset
uspto-grants-1993_05
Patent number
US05214046

Reaction notes

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