(+-)-Tetramisole → Levamisole

HRID 652559

Reaction equation

HRID 652559 reaction equation
COC1C=CC(S(N[C@H](C(O)=O)CCC(O)=O)(=O)=O)=CC=1.[CH:22]1[CH:23]=[CH:24][C:25]([CH:28]2[N:35]=[C:34]3[N:30]([CH2:31][CH2:32][S:33]3)[CH2:29]2)=[CH:26][CH:27]=1>CC(=O)C.O>[CH:22]1[CH:27]=[CH:26][C:25]([C@@H:28]2[N:35]=[C:34]3[N:30]([CH2:31][CH2:32][S:33]3)[CH2:29]2)=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 3913(+-)-TetramisoleHCID 10734242N-[(4-Methoxyphenyl)sulfonyl]-L-glutamic acid

Product 1

HCID 26879LevamisoleYield 125.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A suspension of 31.73 g of L-N-[(4-methoxyphenyl)sulfonyl-glutamic acid (0.1 mol) in 400 ml of 2-propanone and 20 ml of water was stirred and heated till all solid entered solution. Then there were added 20.43 g of tetramisole. The whole was stirred and heated to reflux and additionally stirred at reflux for 10 minutes. The mixture was further stirred for 4 hours while the temperature was allowed to reach room temperature. The precipitate was filtered off, washed with 100 ml of 2-propanone and 5 ml of water and dried under vacuo at 50° C., yielding 25.55 g of levamisole.L-N-[(4-methoxyphenyl)sulfonyl]glutamic acid (salt) (yield 98%) αD20 =-62.4° (c5. 1N HCl); mp. 127.3°-129° C.

Workup

  1. temperatureheated till all solid
  2. stirringThe whole was stirred
  3. temperatureheated
  4. temperatureto reflux
  5. stirringadditionally stirred
  6. temperatureat reflux for 10 minutes
  7. stirringThe mixture was further stirred for 4 hours while the temperature
  8. customto reach room temperature
  9. filtrationThe precipitate was filtered off
  10. washwashed with 100 ml of 2-propanone and 5 ml of water
  11. customdried under vacuo at 50° C.

Sources & evidence

ORD record
ord-39d61556ffe940a39166c99a89a511b3
Source dataset
uspto-grants-1987_06
Patent number
US04672126

Linked notes

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