Acetonitrile → HCID 178491309, compound

HRID 2285734Notes

Reaction equation

HRID 2285734 reaction equation
[C:1](Cl)(=[O:10])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[CH2:12](N1C=CN=C1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH2:24]([N:26](CC)[CH2:27][CH3:28])C.C(#[N:33])C>>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:1]([C:27]2[N:26]=[C:24]([CH2:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:33][CH:28]=2)=[O:10])=[CH:3][CH:4]=1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 7477p-Anisoyl chlorideHCID 8471TriethylamineHCID 779181-Benzylimidazole

Product 1

HCID 178491309HCID 178491309, compound

Procedure

Anisoyl chloride (4.3 ml) was added slowly to a stirred solution of 1-benzylimidazole (5.0 g) in dry acetonitrile (50 ml) keeping the temperature at 25°-30°. After stirring for 1 h. triethylamine (4.4 ml) was added dropwise and the mixture stirred for 18 h. then filtered. The filtrate was concentrated to dryness, and the residue taken up into ether (100 ml) and washed with acetic acid (25%, 3×50 ml), and 2 N sodium carbonate (3×50 ml), then concentrated until the title compound crystallised as a white solid, m.p. 108°-110° (3.1 g).

Workup

  1. customat 25°-30°
  2. additionwas added dropwise
  3. filtrationthen filtered
  4. concentrationThe filtrate was concentrated to dryness
  5. washwashed with acetic acid (25%, 3×50 ml), and 2 N sodium carbonate (3×50 ml)
  6. concentrationconcentrated until the title compound
  7. customcrystallised as a white solid, m.p. 108°-110° (3.1 g)

Sources & evidence

ORD record
ord-71747a5102304c7da6568401b47aa5ae
Source dataset
uspto-grants-1982_04
Patent number
US04324792

Reaction notes

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