Dimethylformamide → HCID 19966024, compound

HRID 977850Notes

Reaction equation

HRID 977850 reaction equation
[H-].[Na+].CN(C)C=O.[CH2:8]([OH:12])[CH2:9][CH2:10][OH:11].S(O[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([S:25][CH3:26])[C:20]=1[N+:27]([O-:29])=[O:28])(C)(=O)=O>CCCCCC.O>[OH:11][CH2:10][CH2:9][CH2:8][O:12][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([S:25][CH3:26])[C:20]=1[N+:27]([O-:29])=[O:28]

Participants

7

Reactant 4

HCID 6228Dimethylformamide2×HCID 104421,3-PropanediolHCID 24758Sodium hydrideHCID 19966062HCID 19966062, compound

Product 1

HCID 19966024HCID 19966024, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

33 mg (0.76 mmol) of sodium hydride (as a 55% w/w suspension in mineral oil) were washed twice with hexane, and then 1 ml of dimethylformamide was added to the suspension. The resulting suspension was cooled in an ice bath, and then 0.8 ml (11 mmol) of 1,3-propanediol was added. The mixture was then stirred for 30 minutes at this temperature and then for 30 minutes at room temperature. 1 ml of a dimethylformamide solution containing the whole of the 2-mesyloxymethyl-6-methylthio-1-nitrobenzene prepared as described in step (i) above was then added to the resulting solution, whilst ice-cooling, and the mixture was stirred for 2 hours at the ice-cooling temperature and then for 1.5 hours at room temperature. At the end of this time, water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic extract was washed with water several times, and then the solvent was removed by distillation under reduced pressure. The resulting residue was subjected to column chromatography through 10 g of silica gel using mixtures of methylene chloride and ethyl acetate in ratios ranging from 10:1 to 8:1 by volume as the eluent, to obtain 95 mg (yield 74%) of the title compound as an oily substance.

Workup

  1. temperatureThe resulting suspension was cooled in an ice bath
  2. waitfor 30 minutes at room temperature
  3. customprepared
  4. additionabove was then added to the resulting solution, whilst ice-
  5. temperaturecooling
  6. temperaturecooling temperature
  7. waitfor 1.5 hours at room temperature
  8. extractionthe mixture was extracted with ethyl acetate
  9. extractionThe organic extract
  10. washwas washed with water several times
  11. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-58ca91cff77a4fb8a37527d99d37c6e5
Source dataset
uspto-grants-1997_03
Patent number
US05614550

Reaction notes

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