Ammonia → HCID 135772691, compound

HRID 458805Notes

Reaction equation

HRID 458805 reaction equation
Br[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH3:15])=[CH:8][C:7]=1[C:16](=O)[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=1)=[O:4].[NH3:27]>CO.ClCCl>[Cl:25][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][C:21]=1[Cl:24])[CH2:17][C:16]1[C:7]2[CH:8]=[C:9]([O:14][CH3:15])[C:10]([O:12][CH3:13])=[CH:11][C:6]=2[NH:5][C:3](=[O:4])[CH2:2][N:27]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 18442580HCID 18442580, compound

Product 1

HCID 135772691HCID 135772691, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

2-Bromo-N-{2-[2-(3,4-dichloro-phenyl)-acetyl]-4,5-dimethoxy-phenyl}-acetamide (5.25 g, 11.39 mmol) was placed at −10° C. under nitrogen. Ammonia in methanol (7N, 55 ml) was added dropwise at −10° C. and the reaction mixture was heated at 40° C. for 2.5 h, and then at reflux (75° C.) for 1 h. The solvent was evaporated under vacuum yielding a yellow solid which was dissolved in dichloromethane and washed with water. The organic phase was dried over magnesium sulfate, filtered and evaporated to dryness. Flashchromatography (dichloromethane/methanol, 18/1) yielded the expected product as a yellow solid (1.5 g, 35%).

Workup

  1. customwas placed at −10° C. under nitrogen
  2. temperatureat reflux (75° C.) for 1 h
  3. customThe solvent was evaporated under vacuum
  4. customyielding a yellow solid which
  5. washwashed with water
  6. dry with materialThe organic phase was dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-14e9002090f24923b1fad076670e3e62
Source dataset
uspto-grants-2007_03
Patent number
US07192950B2

Reaction notes

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