Phenolate Sodium → HCID 13060092, compound

HRID 2164061Notes

Reaction equation

HRID 2164061 reaction equation
Cl.[CH3:2][C:3]1[N:4]2[CH:10]=[C:9]([CH2:11]Cl)[N:8]=[C:5]2[S:6][CH:7]=1.[CH:13]1[CH:18]=[CH:17][C:16]([O-:19])=[CH:15][CH:14]=1.[Na+]>C1COCC1>[CH3:2][C:3]1[N:4]2[CH:10]=[C:9]([CH2:11][O:19][C:16]3[CH:17]=[CH:18][CH:13]=[CH:14][CH:15]=3)[N:8]=[C:5]2[S:6][CH:7]=1

Participants

4

Reactant 2

HCID 4445035Phenolate SodiumHCID 23462418HCID 23462418, compound

Product 1

HCID 13060092HCID 13060092, compoundYield 107.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.4 g of 3-methyl-6-chloromethyl-imidazo-(2,1-b)thiazole hydrochloride, prepared as described in Example 27, is introduced with stirring into a cooled solution of 3.5 g of sodium phenate in 100 ml of THF. After about 1 hour the sodium chloride which precipitates is filtered off, the solvent is evaporated and acidic water is added to the residue. The aqueous solution is extracted, at pH 3-6, with chloroform. The pH is then raised to 7-7.5 and the aqueous solution is again extracted with chloroform. This extract is dried and the solvent is then evaporated to yield 4 g of 3-methyl-6-phenoxymethyl-imidazo-(2,1-b)thiazole; m.p. 190°-192° (methyl-ethyl-ketone).

Workup

  1. additionis introduced
  2. customAfter about 1 hour the sodium chloride which precipitates
  3. filtrationis filtered off
  4. customthe solvent is evaporated
  5. additionacidic water is added to the residue
  6. extractionThe aqueous solution is extracted, at pH 3-6, with chloroform
  7. temperatureThe pH is then raised to 7-7.5
  8. extractionthe aqueous solution is again extracted with chloroform
  9. customThis extract is dried
  10. customthe solvent is then evaporated

Sources & evidence

ORD record
ord-ee460bb6dec74e95bd2ed552d59dc44e
Source dataset
uspto-grants-1979_01
Patent number
US04137320

Reaction notes

Loading…