Triethylamine → 1-(p-cyanophenylmethyl)-5-(2-formylethyl)-1H-imidazole

HRID 568537Notes

Reaction equation

HRID 568537 reaction equation
C(Cl)(=O)C(Cl)=O.[C:7]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:20]([CH2:21][CH2:22][CH2:23][OH:24])=[CH:19][N:18]=[CH:17]2)=[CH:11][CH:10]=1)#[N:8].C(N(CC)CC)C>C(Cl)Cl.CS(C)=O>[C:7]([C:9]1[CH:10]=[CH:11][C:12]([CH2:15][N:16]2[C:20]([CH2:21][CH2:22][CH:23]=[O:24])=[CH:19][N:18]=[CH:17]2)=[CH:13][CH:14]=1)#[N:8]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 136882083-[1-(4-Cyanobenzyl)-1H-imidazol-5-yl]-1-propanol

Product 1

HCID 152947311-(p-cyanophenylmethyl)-5-(2-formylethyl)-1H-imidazole

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 0.14 ml of dimethylsulfoxide in 5 ml of methylene chloride is cooled to -78° under N2 and 0.1 ml of oxalyl chloride is added dropwise. After 30 min, a solution of 0.24 g of 1-(p-cyanophenylmethyl)-5-(3-hydroxypropyl)-1H-imidazole in 1 ml of methylene chloride and 0.2 ml of dimethylsulfoxide is added slowly. The reaction mixture is stirred at -78° for 2 h and 1 ml of triethylamine is added slowly. The reaction mixture is allowed to warm slowly to room temperature, diluted with 30 ml of methylene chloride and washed three times with 10 ml of water. The organic phase is dried over sodium sulfate and evaporated to yield the title compound (a) as an oil, NMR (60 MHZ): δ 5.15 (s, 2H), 9.65 (s, 1H).

Workup

  1. washwashed three times with 10 ml of water
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-debc7f3004c34b7fa0abfcab7c591b40
Source dataset
uspto-grants-1988_03
Patent number
US04728645

Reaction notes

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