Triethylamine → HCID 67606772, compound

HRID 573398Notes

Reaction equation

HRID 573398 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:13])[CH3:12])=[C:6]([N+:14]([O-:16])=[O:15])[C:5]=1[OH:17])(=[O:3])[CH3:2].C(N(CC)CC)C.[CH3:25][N:26]([CH3:36])[C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=1>C(Cl)Cl>[CH3:25][N:26]([CH3:36])[C:27]1[CH:35]=[CH:34][C:30]([C:31]([O:17][C:5]2[C:4]([C:1](=[O:3])[CH3:2])=[CH:9][CH:8]=[C:7]([NH:10][C:11](=[O:13])[CH3:12])[C:6]=2[N+:14]([O-:16])=[O:15])=[O:32])=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 44007824-(Dimethylamino)benzoyl chlorideHCID 19045250HCID 19045250, compound

Product 1

HCID 67606772HCID 67606772, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The imidazole flavonoid was prepared according to scheme 5. To a mixture of N-(4-acetyl-3-hydroxy-2-nitrophenyl)acetamide (1, 1 g, 4.1 mmol, 1.0 eq) and triethylamine (1.5 mL) was added 4-(dimethylamino)benzoyl chloride (2 hydrochloride, 6.3 mmol, 1.5 eq.) in 3 portions at 0° C. Then the mixture was stirred at rt for 3 h. Diluted with DCM (100 mL), washed with 1N HCl (100 mL) and water (50 mL). The organic phase was separated, dried with sodium sulfate, filtered and concentrated to afford gray solid, which was purified by SGC (PE/EA=1/1) to afford (3-acetamido-6-acetyl-2-nitrophenyl 4-(dimethylamino)benzoate (3), 1.2 g, 75%).

Workup

  1. washwashed with 1N HCl (100 mL) and water (50 mL)
  2. customThe organic phase was separated
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford gray solid, which
  7. customwas purified by SGC (PE/EA=1/1)

Sources & evidence

ORD record
ord-5d9447c948ef4e4aa0bc442d0a6d3490
Source dataset
uspto-grants-2015_05
Patent number
US09029561B2

Reaction notes

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