Hydrochloric Acid → HCID 63346583, compound

HRID 2076077Notes

Reaction equation

HRID 2076077 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH:6]2[C:11]2[O:15][N:14]=[C:13]([CH3:16])[N:12]=2)[O:4]CC1.Cl>O1CCCC1>[CH3:16][C:13]1[N:12]=[C:11]([CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:5]2=[O:4])[O:15][N:14]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67095925HCID 67095925, compound

Product 1

HCID 63346583HCID 63346583, compoundYield 20.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5-(1,4-dioxa-spiro[4.5]dec-6-yl)-3-methyl-[1,2,4]oxadiazole (0.67 g, 3.0 mmol), tetrahydrofuran (70 mL), and 3 N hydrochloric acid (35 mL) was stirred at 60° C. for 13 h. The mixture was cooled and extracted with ethyl acetate. The organic layer was successively washed with saturated sodium bicarbonate solution and with brine, dried over sodium sulfate, and evaporated under reduced pressure. The remaining solid was recrystallized from heptane to give the title compound (0.11 g, 20%) as an off-white solid. MS ISP (m/e): 181.1 [(M+H)+]. mp 74-76° C.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was successively washed with saturated sodium bicarbonate solution and with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe remaining solid was recrystallized from heptane

Sources & evidence

ORD record
ord-60e640f0e6654e7da1d67d378fdbf96d
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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