Imidazole → HCID 70351161, compound

HRID 2291994Notes

Reaction equation

HRID 2291994 reaction equation
N1C=CN=C1.Cl.[O:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH:9]=[C:8]1[CH:16]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1C)[N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1.S(Cl)([Cl:31])=O.O1C2C=CC=CC=2C=C1C(C1C=CC=CC=1)O>C(#N)C>[ClH:31].[O:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH:9]=[C:8]1[CH:16]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 24386Thionyl ChlorideHCID 15150176α-Phenyl-2-benzofuranmethanolHCID 21277788HCID 21277788, compound

Product 1

HCID 70351161HCID 70351161, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To 0.08 moles of imidazole in 70 ml of acetonitrile, at the temperature of 10 C., 0.02 moles of thionylchloride are added, followed by 1 hour rest, and then 0.02 moles of (benzofuran-2-yl)phenylmethanol are added in 20 ml of acetonitrile. The reaction admixture is kept 24 hours at ambient temperature and then concentrated to dryness. The residue is taken up with ethylether, washed first with 2% sodium hydrate solution and then with water: the hydrochloride is obtained from the ethereal solutions using 5% hydrochloric acid, then an oil is obtained by alkalinization with 5% NaOH, which is extracted with ethylether. The ethereal extract is washed, made anhydrous and saturated with gaseous HCl: the precipitate thus obtained is crystallized from isopropanol: m.p. 205°-207° C. (dec.).

Workup

  1. waitThe reaction admixture is kept 24 hours at ambient temperature
  2. concentrationconcentrated to dryness
  3. washwashed first with 2% sodium hydrate solution

Sources & evidence

ORD record
ord-7d1c411564f147e6b827747a4042f182
Source dataset
uspto-grants-1989_01
Patent number
US04800208

Reaction notes

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