Hydrochloric Acid → HCID 58097574, compound

HRID 386671Notes

Reaction equation

HRID 386671 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]([NH:31]C(=O)C)=[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.Cl>C(O)C>[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

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68751459HCID 68751459, compound

Product 1

HCID 58097574HCID 58097574, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-[(4-(imidazol-1-yl)-phenyl]-3-benzyloxy-6-acetamido-4H-1-benzopyran-4-one (7 g; 15.5 mmol) was suspended in ethanol (250 mL), HCl 4N (16 mL; 62 mmol) was added and the mixture refluxed for 24 hours. After cooling, the reaction was concentrated and the precipitate was filtered off. The crude was suspended in diisopropyl ether, filtered and dried to give the titled compound as light yellow solid. 1H-NMR (d6-DMSO): 9.91 (s, 1H); 8.44 (d, 1H); 8.22 (d, 2H); 7.90 (d, 3H); 7.78 (d, 2H); 7.33 (d, 1H); 7.32 (m, 6H); 5.16 (s, 2H); MS (EI) 410 (M+1), 319 (M-91).

Workup

  1. temperaturethe mixture refluxed for 24 hours
  2. temperatureAfter cooling
  3. concentrationthe reaction was concentrated
  4. filtrationthe precipitate was filtered off
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-8c2640f99fa3477ebee11044a0edcec4
Source dataset
uspto-grants-2013_02
Patent number
US08372866B2

Reaction notes

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