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

HRID 477984Notes

Reaction equation

HRID 477984 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): δ5.15 (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-0fe8c443d4b8496780c2affe9d7029b3
Source dataset
uspto-grants-1989_12
Patent number
US04889861

Reaction notes

Loading…