2-Bromo-2',5'-dimethoxyacetophenone → HCID 53987506, compound

HRID 357596Notes

Reaction equation

HRID 357596 reaction equation
[C:1]([NH:4][N:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[NH:3])[NH2:2].[CH3:13][O:14][C:15]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:16]=1[C:17](=O)[CH2:18]Br>C(O)C>[NH2:3][C:1]1[N:4]([N:5]=[CH:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:18]=[C:17]([C:16]2[CH:21]=[C:22]([O:25][CH3:26])[CH:23]=[CH:24][C:15]=2[O:14][CH3:13])[N:2]=1

Participants

4

Reactant 2

HCID 709972-Bromo-2',5'-dimethoxyacetophenoneHCID 178513139HCID 178513139, compound

Product 1

HCID 53987506HCID 53987506, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1.62 g (0.01 mol) of benzaldehyde guanylhydrazone and 1.34 g of 2,5-dimethoxyphenacyl bromide (Aldrich, Buchs, Switzerland, 97%, Cat. no. 10,458-2) in 5 ml of ethanol is boiled under reflux for 45 minutes. After cooling, the product that has crystallized out is filtered off with suction and recrystallized from ethanol. In that manner there is obtained the title compound, m.p. 180°-181° C., 1H-NMR (DMSO): δ=8.62 (s, 1H); 7.97 (m, 2H); 7.90 (s, 1H); 7.42-7.60 (m, 4H); 6.95 (d, 1H); 6.76 (m, 1H); 6.18 (s, 2H); 3.9 (s, 3H); 3.73 (s, 3H).

Workup

  1. temperatureunder reflux for 45 minutes
  2. temperatureAfter cooling
  3. customthe product that has crystallized out
  4. filtrationis filtered off with suction
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-def1b127405b47fdbd8cedfa021e7ea9
Source dataset
uspto-grants-1998_11
Patent number
US05840911

Reaction notes

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