Thionyl Chloride → HCID 23321854, compound

HRID 280221Notes

Reaction equation

HRID 280221 reaction equation
O[CH2:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][CH2:8][C:9]2[N:14]3[CH:15]=[N:16][CH:17]=[C:13]3[CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.S(Cl)([Cl:22])=O>>[Cl:22][CH2:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][CH2:8][C:9]2[N:14]3[CH:15]=[N:16][CH:17]=[C:13]3[CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 23321861HCID 23321861, compound

Product 1

HCID 23321854HCID 23321854, compound

Procedure

5-[p-(hydroxymethyl)phenethyl]imidazo[1,5-a]pyridine (2.52 g) is refluxed in 20 ml of thionyl chloride for 2 hours. Excess thionyl chloride is evaporated and the residue is partitioned between ethyl acetate and dilute sodium bicarbonate solution. The organic phase is dried over sodium sulfate and evaporated to yield 5-[p-(chloromethyl)-phenethyl]imidazo[1,5-a]pyridine.

Workup

  1. customExcess thionyl chloride is evaporated
  2. customthe residue is partitioned between ethyl acetate and dilute sodium bicarbonate solution
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-2099b84af2a84e15bb541d2beb82c31b
Source dataset
uspto-grants-1986_05
Patent number
US04588732

Reaction notes

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