Acetonitrile → HCID 178465564, compound

HRID 386670Notes

Reaction equation

HRID 386670 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[O:13][C:14]4[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][C:15]=4[C:16](=[O:26])[C:17]=3[O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[C:32](#[N:34])[CH3:33]>>[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[O:13][C:14]4[CH:30]=[CH:29][C:28]([NH:31][C:32](=[NH:34])[CH3:33])=[CH:27][C:15]=4[C:16](=[O:26])[C:17]=3[O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 58097574HCID 58097574, compound

Product 1

HCID 178465564HCID 178465564, compoundYield 73%

Conditions

Temperature
0 °C

Procedure

2-[(4-(imidazol-1-yl)-phenyl]-3-benzyloxy-6-amino-4H-1-benzopyran-4-one (3 g; 6.22 mmol) was suspended in acetonitrile (50 mL) and cooled at 0° C. HCl was bubbled into the solution upon saturation. The reaction was then stirred for 4 hours at r.t., upon completion, H2O (20 mL) was added and the acetonitrile removed under vacuum. The solution was then brought to pH=9 with NaOH 2N, the precipitate was filtered off and dried to give the titled compound as a bright yellow solid. Yield: 73%. TLC: (9/1 Chloroform/Methanol) Rf: 0.6.

Workup

  1. customHCl was bubbled into the solution upon saturation
  2. additionwas added
  3. customthe acetonitrile removed under vacuum
  4. filtrationthe precipitate was filtered off
  5. customdried

Sources & evidence

ORD record
ord-1441483351074a40bdf9209f95e30903
Source dataset
uspto-grants-2013_02
Patent number
US08372866B2

Reaction notes

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