Formamide → Ethyl 6,7-dihydrothiazolo[5,4-c]pyridine-5(4h)-carboxylate

HRID 459444Notes

Reaction equation

HRID 459444 reaction equation
P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:2].O.C(OCC)C.Cl[CH:22]1[C:27](=O)[CH2:26][CH2:25][N:24]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:23]1.[CH:34]([NH2:36])=O>C(O)CCC>[CH2:32]([O:31][C:29]([N:24]1[CH2:25][CH2:26][C:27]2[N:36]=[CH:34][S:2][C:22]=2[CH2:23]1)=[O:30])[CH3:33]

Participants

7

Reactant 5

HCID 713FormamideHCID 962WaterHCID 3283Diethyl EtherHCID 14817Phosphorus sulfide (P2S5)HCID 132261553-Chloro-1-ethoxycarbonylpiperidin-4-one

Product 1

HCID 17842604Ethyl 6,7-dihydrothiazolo[5,4-c]pyridine-5(4h)-carboxylate

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Phosphorus pentasulfide (500 g) was suspended in formamide (3,000 ml) with ice cooling, and the suspension was stirred overnight. Water and diethyl ether were added to the reaction mixture, and an organic layer was separated and dried over anhydrous magnesium sulfate, and the solvent was distilled off to obtain a yellow oil. After the oil was dissolved in n-butanol (350 ml), and 3-chloro-1-ethoxycarbonylpiperidin-4-one (150 g) synthesized according to the process described in literature (Tetrahedron, 1983, Vol. 39, p. 3767) was added to the solution, the resultant mixture was stirred at 100° C. for 2.5 hours. The reaction mixture was filtered through Celite. The resultant filtrate was washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated saline, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (dichloromethane-ethyl acetate:hexane=1:2) to obtain the title compound (79.0 g) as a brown oil.

Workup

  1. customan organic layer was separated
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off
  4. customto obtain a yellow oil
  5. additionwas added to the solution
  6. filtrationThe reaction mixture was filtered through Celite
  7. washThe resultant filtrate was washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated saline
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled off under reduced pressure
  10. customthe residue was purified by column chromatography on silica gel (dichloromethane-ethyl acetate:hexane=1:2)

Sources & evidence

ORD record
ord-995ad382d30a4a1d9ae07b988211f83f
Source dataset
uspto-grants-2007_03
Patent number
US07192968B2

Reaction notes

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