Acetone → HCID 12795056, compound

HRID 648000Notes

Reaction equation

HRID 648000 reaction equation
S(OC)(OC)(=O)=O.[OH:8][CH2:9][CH2:10][CH2:11][N:12]1[CH:16]=[CH:15][CH:14]=[C:13]1N(C)C.C(Cl)Cl.[C-]#[N:24].[Na+].C[C:27]([CH3:29])=O>O.CO>[OH:8][CH2:9][CH2:10][CH2:11][N:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[CH2:29][C:27]#[N:24]

Participants

8

Reactant 5

HCID 180AcetoneHCID 6344DichloromethaneHCID 6497Dimethyl SulfateHCID 8929Sodium CyanideHCID 20484041HCID 20484041, compound

Product 1

HCID 12795056HCID 12795056, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Dimethyl sulfate (44.2 g, 0.362 moles) is added to a stirred and cooled solution of 1-(3-hydroxypropyl)-2-dimethylaminopyrrole (57 g, 0.313 moles) in acetone (285 ml), maintained in an atmosphere of nitrogen, at a rate such that the reaction temperature does not exceed 4° C. The reaction is then allowed to come to room temperature at which point stirring is continued for a further 1 hour. The reaction is complete (t.l.c., silica gel, CH2Cl2 --MeOH; 90:10) at this time and a solution of sodium cyanide (33.4 g., 1.28 moles) in water (74 ml.) is added. The apparatus is equipped to permit distillation and the reaction is heated to 95° during which time a distillate (ca. 275 ml.) is collected. The reaction is then heated at gentle reflux for 0.5 hours and 150 ml. water is added. the product is extracted into dichloromethane (4×200 ml.), the extract is washed with dilute sodium chloride solution and then dried over sodium sulfate. The solvent is removed in vacuo and the oily residue (51 g) is purrified by column chromatography over silica gel to give 38.1 g (74%) 1-(3-hydroxypropyl)pyrrol-2-acetonitrile (Formula (XVII) where n is 1) which is contained in the hexane-ethyl acetate (85:15) eluate. The product on distillation, b.p. 146°/0.15 mm is analytically pure and exhibited the following physical characteristics:

Workup

  1. temperaturemaintained in an atmosphere of nitrogen, at a rate such that the reaction temperature
  2. customdoes not exceed 4° C
  3. customto come to room temperature at which point
  4. stirringstirring
  5. customThe apparatus is equipped
  6. distillationdistillation
  7. temperaturethe reaction is heated to 95° during which time a distillate (ca. 275 ml.)
  8. customis collected
  9. temperatureThe reaction is then heated
  10. temperatureat gentle reflux for 0.5 hours
  11. additionwater is added
  12. extractionthe product is extracted into dichloromethane (4×200 ml.)
  13. washthe extract is washed with dilute sodium chloride solution
  14. dry with materialdried over sodium sulfate
  15. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-a16adf75d6b74b89acf68ef5c5c5ccd0
Source dataset
uspto-grants-1983_10
Patent number
US04410534

Reaction notes

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