Dimethyl Sulfoxide → 5-(p-Formylphenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine

HRID 477991Notes

Reaction equation

HRID 477991 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]2[N:24]3[CH:25]=[N:26][CH:27]=[C:23]3[CH2:22][CH2:21][CH2:20]2)=[CH:15][CH:14]=1.C(N(CC)CC)C>C(Cl)Cl>[CH:12]([C:13]1[CH:14]=[CH:15][C:16]([CH:19]2[N:24]3[CH:25]=[N:26][CH:27]=[C:23]3[CH2:22][CH2:21][CH2:20]2)=[CH:17][CH:18]=1)=[O:11]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 136882185-(p-Hydroxymethylphenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine

Product 1

HCID 140971985-(p-Formylphenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 0.16 ml of dimethylsulfoxide in 16 ml of methylene chloride is cooled to -70° under nitrogen and 0.17 g of oxalyl chloride is added dropwise. The reaction mixture is stirred for 30 min and 0.24 g of 5-(p-hydroxymethylphenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine in 4 ml of methylene chloride is added slowly. The reaction mixture is stirred for 2 h at -70°, 0.8 ml of triethylamine is added dropwise, and the reaction mixture is allowed to warm slowly to room temperature. The reaction mixture is diluted with 20 ml of methylene chloride, washed with water, dried over sodium sulfate and evaporated to yield the title compound which is purified by conversion to the fumaric acid salt, m.p. 131°.

Workup

  1. stirringThe reaction mixture is stirred for 2 h at -70°
  2. washwashed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-4df6046b2eb242189db1b67db3a1403c
Source dataset
uspto-grants-1989_12
Patent number
US04889861

Reaction notes

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