(+-)-Tetramisole → Levamisole

HRID 652559

反応式

HRID 652559 の反応式
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

参加物

5

反応物 2

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

生成物 1

HCID 26879Levamisole収率 125.1%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 962Water溶媒

実験手順

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.

後処理

  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.

出典と根拠

ORDレコード
ord-39d61556ffe940a39166c99a89a511b3
出典データセット
uspto-grants-1987_06
特許番号
US04672126

関連ノート

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