Benzoyl chloride → HCID 59443459, compound

HRID 1035623Notes

Reaction equation

HRID 1035623 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[C:8]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:20][CH3:21])[CH:16]=3)[CH:11]=2)[CH:7]=[CH:6][C:4]=1[NH2:5].[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3]1[CH:9]=[C:8]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:20][CH3:21])[CH:16]=3)[CH:11]=2)[CH:7]=[CH:6][C:4]=1[NH:5][C:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 10340Sodium CarbonateHCID 59443493HCID 59443493, compound

Product 1

HCID 59443459HCID 59443459, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methoxy-4-(6-methoxy-2-naphthyl)aniline (82 mg, 0.29 mmol, 1 eq) in 10 ml of dry dichloromethane are added benzoyl chloride (0.1 ml, 123 mg, 0.88 mmol, 3 eq) and trace amounts of DMAP. After stirring for 18 h at RT, the reaction mixture is stopped by adding a 2% sodium carbonate solution, the phases are separated, and the aqueous phase is extracted with dichloromethane. The combined organic phases are dried over magnesium sulfate, filtered and concentrated in vacuum on a rotary evaporator. Purification by column chromatography with a gradient of hexane/ethyl acetate 9/1 to 1/1 yielded the desired product in a yield of 90% (101 mg).

Workup

  1. customthe phases are separated
  2. extractionthe aqueous phase is extracted with dichloromethane
  3. dry with materialThe combined organic phases are dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum on a rotary evaporator
  6. customPurification by column chromatography with a gradient of hexane/ethyl acetate 9/1 to 1/1

Sources & evidence

ORD record
ord-591ad018db9d47e092dce65c839907a7
Source dataset
uspto-grants-2013_10
Patent number
US08546392B2

Reaction notes

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