Benzyl Alcohol → HCID 67771393, compound

HRID 1195741Notes

Reaction equation

HRID 1195741 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Cl:11][C:12]1[CH:13]=[C:14](Cl)[C:15]2[N:16]([CH:18]=[C:19]([CH3:21])[N:20]=2)[CH:17]=1.Cl>CN(C)C=O>[ClH:11].[CH2:3]([O:10][C:14]1[C:15]2[N:16]([CH:18]=[C:19]([CH3:21])[N:20]=2)[CH:17]=[C:12]([Cl:11])[CH:13]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 54442238HCID 54442238, compound

Product 1

HCID 67771393HCID 67771393, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-40 °C

Procedure

1.8 g commercial 80% sodium hydride in paraffin is added in small portions at room temperature to 5.4 ml benzyl alcohol dissolved in 300 ml dry dimethylformamide. The benzylate solution is stirred for a further 2 hours. Thereafter it is cooled to -40° C., mixed with 10.0 g 6,8-dichloro-2-methyl-imidazo[1,2-a]pyridine and stirred for a further 4 hours. The temperature is allowed to rise gradually to 12° C. and the mixture is stirred at this temperature for 48 hours. Thereafter the solution is poured onto 1.5 kg icewater, the solution brought to pH=7 with 1 N-HCl and extracted 3×with 100 ml ethyl acetate each time. The combined extracts are dried with sodium sulfate and evaporated to dryness on the rotary evaporator. After dissolution in 100 ml 2-propanol, the title compound is precipitated by addition of saturated HCl-ether solution. After the precipitate has been filtered off under suction, it is recrystallized twice from isopropanol, 4.5 g of the title compound of m.p. 180°-182° C. being obtained.

Workup

  1. stirringstirred for a further 4 hours
  2. customto rise gradually to 12° C.
  3. stirringthe mixture is stirred at this temperature for 48 hours
  4. additionThereafter the solution is poured onto 1.5 kg icewater
  5. extractionextracted 3×with 100 ml ethyl acetate each time
  6. dry with materialThe combined extracts are dried with sodium sulfate
  7. customevaporated to dryness on the rotary evaporator
  8. dissolutionAfter dissolution in 100 ml 2-propanol
  9. customthe title compound is precipitated by addition of saturated HCl-ether solution
  10. filtrationAfter the precipitate has been filtered off under suction, it
  11. customis recrystallized twice from isopropanol, 4.5 g of the title compound of m.p. 180°-182° C.
  12. custombeing obtained

Sources & evidence

ORD record
ord-90a8ed52e1a849a5879ac474a17ccfb8
Source dataset
uspto-grants-1992_05
Patent number
US05112834

Reaction notes

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