p-Toluenesulfonic acid → p-Toluenesulfonate

HRID 1632145Notes

Reaction equation

HRID 1632145 reaction equation
Cl[CH2:2][CH2:3][CH2:4][NH:5][C:6]([NH:8][C:9]1[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:16])=[O:7].[CH2:17]([NH2:20])[C:18]#[CH:19].[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27]([OH:30])(=[O:29])=[O:28])=[CH:23][CH:22]=1>C(#N)C>[CH3:16][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]([CH3:15])[C:9]=1[NH:8][C:6]([NH:5][CH2:4][CH2:3][CH2:2][NH:20][CH2:17][C:18]#[CH:19])=[O:7].[CH3:31][C:21]1[CH:22]=[CH:23][C:24]([S:27]([O-:30])(=[O:29])=[O:28])=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 239041PropargylamineHCID 13326597HCID 13326597, compound

Product 2

HCID 85570p-ToluenesulfonateHCID 13326599HCID 13326599, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 65 grams of N-(3-chloropropyl)-N'-(2,6-dimethylphenyl)urea, 350 ml. of acetonitrile, and 50 grams of propargylamine was refluxed for 19 hours. The reaction mixture was filtered and the filtrate was evaporated to dryness in vacuo. The residue was dissolved in chloroform and extracted with 250 ml. of 20% hydrochloric acid. The acid extract was cooled and made basic with 50% sodium hydroxide solution. The mixture was extracted with dichloromethane. After drying over magnesium sulfate, the dichloromethane was removed in vacuo to obtain a solid residue, m.p. 139°-143° C. The solid was treated with p-toluenesulfonic acid to obtain the salt. Recrystallization from ethanol-ether afforded N-(2,6-dimethylphenyl)-N'-[3-(2-propynylamino)propyl]urea, 4-methylbenzenesulfonate, m.p. 143°-144.5° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated to dryness in vacuo
  3. dissolutionThe residue was dissolved in chloroform
  4. extractionextracted with 250 ml
  5. extractionThe acid extract
  6. temperaturewas cooled
  7. extractionThe mixture was extracted with dichloromethane
  8. dry with materialAfter drying over magnesium sulfate
  9. customthe dichloromethane was removed in vacuo
  10. customto obtain a solid residue, m.p. 139°-143° C
  11. customto obtain the salt
  12. customRecrystallization from ethanol-ether

Sources & evidence

ORD record
ord-d86ad8723a7943489c2ec534b4c9ed6e
Source dataset
uspto-grants-1984_10
Patent number
US04474707

Reaction notes

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