Ammonium Chloride → HCID 67545412, compound

HRID 885462Notes

Reaction equation

HRID 885462 reaction equation
[C:1]([C:3]1[CH:13]=[C:7]2[C:8](N[C:11](=[O:12])[C:6]2=[CH:5][CH:4]=1)=[O:9])#[N:2].[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([Mg]Br)=[CH:18][CH:17]=1.[Cl-].[NH4+]>ClCCl>[OH:9][CH2:8][C:7]1[CH:13]=[C:3]([CH:4]=[CH:5][C:6]=1[C:11](=[O:12])[C:19]1[CH:20]=[CH:21][C:16]([O:15][CH3:14])=[CH:17][CH:18]=1)[C:1]#[N:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 121983335-cyanophthalimideHCID 178491912HCID 178491912, compound

Product 1

HCID 67545412HCID 67545412, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

20.0 g (125.6 mmol) of 5-cyanophthalimide was dissolved in 200 ml of anhydrous dichloromethane. The solution was cooled to −78° C., and 188 ml of 4-methoxyphenylmagnesium bromide (1 M in THF, 188 mmol) was added dropwise. The mixture was raised to room temperature and stirred for 16 hrs, followed by addition of a saturated ammonium chloride solution. An organic layer was dried over anhydrous magnesium sulfate, and filtered. The solvent was evaporated under reduced pressure, thereby yielding a yellow compound, represented by Formula 3. The compound thus obtained was used in the next reaction without further purification.

Workup

  1. temperatureThe mixture was raised to room temperature
  2. dry with materialAn organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customThe solvent was evaporated under reduced pressure
  5. customyielding a yellow compound
  6. customThe compound thus obtained
  7. customwas used in the next reaction without further purification

Sources & evidence

ORD record
ord-91e2ca74269f43048a1ee1fb89d2347d
Source dataset
uspto-grants-2012_08
Patent number
US08242159B2

Reaction notes

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