Hydrochloric Acid → Levamisole

HRID 652555

Reaction equation

HRID 652555 reaction equation
[OH-].[Na+].[CH:3]1[CH:4]=[CH:5][C:6]([CH:9]2[N:16]=[C:15]3[N:11]([CH2:12][CH2:13][S:14]3)[CH2:10]2)=[CH:7][CH:8]=1.Cl.Cl>O>[CH:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[N:16]=[C:15]3[N:11]([CH2:12][CH2:13][S:14]3)[CH2:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68628Tetramisole Hydrochloride

Product 1

HCID 26879LevamisoleYield 121.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

A mixture containing 11.39 kg of L-N-[(4-methoxyphenyl)sulfonyl]glutamic acid (35.9 mol), 61 l of water, 3.77 l sodium hydroxide 19.5 molar aqueous solution (73.5 mol) and 16.61 kg of tetramisole hydrochloride (69 mol) was warmed up to 40° C. The homogeneous mixture 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 17.15 kg of levamisole.L-N-[(4-methoxyphenyl)sulfonyl]glutamic acid (salt) (yield: 95%); αD20 =65.1° (c5, 1N HCl); mp. 127.9°-129.4° 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-d6ac48afc5374a53b505ff34ed545656
Source dataset
uspto-grants-1987_06
Patent number
US04672126

Linked notes

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