Hydrochloric Acid → Tetramisole Hydrochloride

HRID 2419536

反応式

HRID 2419536 の反応式
[ClH:1].O[CH:3]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:4][N:5]1[CH2:9][CH2:8][S:7][C:6]1=[NH:10].CC1C=CC(S(O)(=O)=O)=CC=1.[Cl-].[Na+].S(=O)(=O)(O)O.[OH-].[Na+].C(=O)([O-])[O-].[K+].[K+]>O.C1(C)C=CC=CC=1>[CH2:9]1[N:5]2[C:6](=[N:10][CH:3]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:4]2)[S:7][CH2:8]1.[ClH:1]

参加物

9

反応物 6

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 8665918126-02-8

生成物 1

HCID 68628Tetramisole Hydrochloride収率 92.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 1140Toluene溶媒

反応条件

温度
50 °C

実験手順

A laboratory pressure bottle is charged with 92 ml. of 37% hydrochloric acid, cooled to 0°-5° C., and a mixture consisting of 79.0 g. (0.2 mole) of dl-3-(β-hydroxyphenethyl)-2-iminothiazolidine-p-toluene sulfonate and 40.4 g. (0.69 mole) of sodium chloride is added. The mixture is cooled to 0°-5° C., and 89.2 g. of 97% sulfuric acid (0.875 mole) is added. The pressure bottle is closed, and the contents heated at 50° C. for 20 hours. The reaction mixture is cooled and added to a mixture of 200 ml. water and 250 ml. of toluene. The mixture is agitated at 20°-30° C. and 50% sodium hydroxide solution is added thereto dropwise to adjust the pH to 6. The mixture is heated to 50°-55° C., 40.0 g. of anhydrous potassium carbonate is added quickly, and the mixture is stirred at 50°-55° C. for 2 hours. At the end of this time, an additional 100 ml. of water is added, the lower aqueous layer separated, and the organic layer clarified. The clarified organic layer is treated with a solution of isopropanolic hydrogen chloride below 40° C. to the point where Congo Red test paper changes from red to blue. The reaction mixture is then cooled to 10° C., the precipitate is separated by filtration, and filter cake washed with 100 ml. of ambient temperature isopropanol. The product is air dried to constant weight to obtain 44.4 g. (92.5% yield) of dl tetramisole hydrochloride, compound VII. The product contains less than 0.1% of the styryl impurity, VIII.

後処理

  1. additionA laboratory pressure bottle is charged with 92 ml
  2. temperatureThe mixture is cooled to 0°-5° C.
  3. customThe pressure bottle is closed
  4. temperatureThe reaction mixture is cooled
  5. additionadded to a mixture of 200 ml
  6. temperatureThe mixture is heated to 50°-55° C.
  7. stirringthe mixture is stirred at 50°-55° C. for 2 hours
  8. customthe lower aqueous layer separated
  9. additionThe clarified organic layer is treated with a solution of isopropanolic hydrogen chloride below 40° C. to the point where Congo Red test paper changes from red to blue
  10. temperatureThe reaction mixture is then cooled to 10° C.
  11. customthe precipitate is separated by filtration
  12. filtrationfilter cake
  13. washwashed with 100 ml
  14. customof ambient temperature
  15. customdried to constant weight
  16. customto obtain 44.4 g

出典と根拠

ORDレコード
ord-bb8ca60974764b2a81d1da734edcbf38
出典データセット
uspto-grants-1978_08
特許番号
US04107170

関連ノート

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