Diethyl Ether → Tebatizole

HRID 461777Notes

Reaction equation

HRID 461777 reaction equation
[CH3:1][C:2]([C:5]([CH2:7]Cl)=O)([CH3:4])[CH3:3].[CH3:9][N:10]1[CH2:15][CH2:14][N:13]([C:16]([NH2:18])=[S:17])[CH2:12][CH2:11]1.C(OCC)C>C(O)C>[CH3:9][N:10]1[CH2:15][CH2:14][N:13]([C:16]2[S:17][CH:7]=[C:5]([C:2]([CH3:4])([CH3:3])[CH3:1])[N:18]=2)[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 835721-ChloropinacoloneHCID 21130864-Methylpiperazine-1-carbothioamide

Product 1

HCID 3085056Tebatizole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.34 g of chloropinacoline are dissolved in 15 cc of absolute ethanol. After the addition of 1.6 g of 4-methyl-1-piperazinyl-thiocarboxamide, the mixture is heated to the boil on a water bath for 1 hour. Cooling is then effected and diethyl ether is added until the mixture remains turbid. The precipitated crystals are filtered off and recrystallized from ethanol. The resulting 2-(4-methyl-1-piperazinyl)-4-tert.butyl-thiazole hydrochloride has an M.P. of 206°. The base liberated from its hydrochloride in known manner by treatment with an aqueous sodium hydroxide solution has a B.P. of 97°-99°/0.2 mm Hg.

Workup

  1. temperaturethe mixture is heated to the boil on a water bath for 1 hour
  2. temperatureCooling
  3. filtrationThe precipitated crystals are filtered off
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-4fbe36d5628d44b490376f262fb0ccdf
Source dataset
uspto-grants-1977_12
Patent number
US04064244

Reaction notes

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