Thiazole → HCID 59831170, compound

HRID 462005Notes

Reaction equation

HRID 462005 reaction equation
[H-].[Na+].OC[CH:5]1[O:9][CH2:8][N:7]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:6]1.S1C=CN=[CH:15]1>O1CCCC1>[CH2:15]=[C:8]1[N:7]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:6][CH2:5][O:9]1

Participants

5

Reactant 3

HCID 9256ThiazoleHCID 24758Sodium hydrideHCID 121778(3-tert-Butyl-1,3-oxazolidin-5-yl)methanol

Product 1

HCID 59831170HCID 59831170, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

This example illustrates the preparation of the compounds of formula III, via the procedure described in the Application of Berkoz, Lewis and Muchowski, Ser. No. 706,412, filed on even date herewith. In this example 0.012 mole of sodium hydride (50% mineral oil) is stirred in 50 ml. of tetrahydrofuran; under nitrogen, and 0.02 mole of 5-hydroxymethyl-N-t-butyloxazolidine is added. The mixture is then warmed to 50° C until reaction ceases (about 30 minutes) and then cooled to room temperature. 0.01 Mole of 2-ethylsulfinyl-5-[2-(endobicyclo[3.1.0]hex-6-yl)ethylaminocarbonyl]thiazole in 50 ml. of tetrahydrofuran is then added. The mixture is stirred for four hours at room temperature and then poured into 200 ml. of ethyl acetate, then washed with water; dried over anhydrous magnesium sulfate and filtered. The filtrate is evaporated under vacuum affording a crude residue of 5-(5-[2-endobicyclo[3.1.0]hex-6-yl)ethylaminocarbonyl]thiazol-2-yloxy)methylene-N-t-butyloxazolidine, which is then dissolved in diethyl ether (100 ml.) and hydrogen chloride gas passed over the surface with rapid stirring until no more precipitate is formed. The precipitate is filtered off, washed with ether, then recrystallized from propanol-diethyl ether mixture. The crystals are filtered off and dried under vacuum affording 5-(5-[2-endobicyclo[3.1.0]hex-6-yl)ethylaminocarbonyl]thiazol-2-yloxy)methylene-N-t-butyloxazolidine hydrochloride.

Workup

  1. temperaturecooled to room temperature
  2. additionpoured into 200 ml
  3. washof ethyl acetate, then washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe filtrate is evaporated under vacuum

Sources & evidence

ORD record
ord-ba2855a16fb54f4d94b5dc1b73494e1a
Source dataset
uspto-grants-1977_12
Patent number
US04064258

Reaction notes

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