Hydrochloric Acid → Levamisole

HRID 652557

Reaction equation

HRID 652557 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([CH:7]2[N:14]=[C:13]3[N:9]([CH2:10][CH2:11][S:12]3)[CH2:8]2)=[CH:5][CH:6]=1.Cl.Cl>O>[CH:1]1[CH:6]=[CH:5][C:4]([C@@H:7]2[N:14]=[C:13]3[N:9]([CH2:10][CH2:11][S:12]3)[CH2:8]2)=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68628Tetramisole Hydrochloride

Product 1

HCID 26879LevamisoleYield 124.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
45 °C

Procedure

A solution of 15.65 kg of levamisole.L-N-[(4-methoxyphenyl)sulfonyl]glutamic acid (salt) (30.02 mol) dissolved in 20.3 l water and 3,15 l sodium hydroxide 19.5 molar aqueous solution was extracted with 30.4 l of methylbenzene at 40° C. and the aqueous layer was washed with 7.5 l methylbenzene. Weighing of the combined water layers and determination of the concentration of the di-sodium salt of L-N-[(4-methoxyphenyl)sulfonyl]glutamic acid yields a 97% amount of di-sodium salt of L-N-[(4-methoxyphenyl)sulfonyl]glutamic acid. To the combined water layers were added 25.2 l water and 13.48 kg of tetramisole hydrochloride. After warming up at about 45° C. the aqueous solution was adjusted to pH 4.2 with hydrochloric acid and cooled at 15° C. After 18 hours the precipitate was filtered off, washed and dried under vacuo at 50° C. yielding 14.27 kg of levamisole.L-N-[(4-methoxyphenyl)sulfonyl]glutamic acid (salt) (yield: 97.7%); αD20 =- 64.1 (c5. 1N HCl); mp. 127.8°-129.3° C..

Workup

  1. temperaturecooled at 15° C
  2. filtrationAfter 18 hours the precipitate was filtered off
  3. washwashed
  4. customdried under vacuo at 50° C.

Sources & evidence

ORD record
ord-15990f19218046059126ccabc67fb96d
Source dataset
uspto-grants-1987_06
Patent number
US04672126

Linked notes

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