Hydrochloric Acid → HCID 19904266, compound

HRID 2372437Notes

Reaction equation

HRID 2372437 reaction equation
[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][Mg]Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C(C2C=CC=CC=2)CCl)C=CC=CC=1.[Mg].[CH2:33]([N:40]1[C:44]([CH:45]=[O:46])=[CH:43][N:42]=[CH:41]1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.Cl>C(OCC)C>[CH2:33]([N:40]1[C:44]([CH:45]([OH:46])[CH2:8][CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:43][N:42]=[CH:41]1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 597525HCID 597525, compoundHCID 27732391-Benzyl-1H-imidazole-5-carboxaldehydeHCID 5462224MagnesiumHCID 178479004HCID 178479004, compound

Product 1

HCID 19904266HCID 19904266, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

The Gringnard reagent, diphenylethanyl magnesium chloride, is prepared by the usual way from diphenylethanylchloride (0.01 mol) and magnesium turnings (0.01 mol) in dry diethylether (30 ml). 1-benzyl-5-imidazole aldehyde (0.005 mol) is dissolved in dry diethylether and the Grignard reagent is added dropwise to the solution. The reaction mixture is refluxed for 3 hours. The reaction is then poured into 2N hydrochloric acid and extracted with diethylether. The water phase is made basic with sodium hydroxide and then extracted with ethyl acetate. The ethyl acetate phase is dried and evaporated. The residue is purified by flash-chromatography eluating with methylene chloride-methanol mixture (9.5:0.5). M.p. of the product as base is 188°-190° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 3 hours
  2. extractionextracted with diethylether
  3. extractionextracted with ethyl acetate
  4. dry with materialThe ethyl acetate phase is dried
  5. customevaporated
  6. customThe residue is purified by flash-chromatography
  7. customis 188°-190° C.

Sources & evidence

ORD record
ord-d4998a79709845d5b44fcc6ba5b828bb
Source dataset
uspto-grants-1992_03
Patent number
US05098923

Reaction notes

Loading…