Pivaloyl chloride → HCID 58828609, compound

HRID 602319Notes

Reaction equation

HRID 602319 reaction equation
[NH:1]([C:8]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:9]=1[C:10]([NH2:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19](Cl)(=O)[C:20]([CH3:23])([CH3:22])[CH3:21]>ClC(Cl)C>[C:20]([C:23]1[N:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:8]2[C:9]([C:10](=[O:11])[N:12]=1)=[CH:13][CH:14]=[C:15]([O:17][CH3:18])[CH:16]=2)([CH3:22])([CH3:21])[CH3:19]

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 66645954HCID 66645954, compound

Product 1

HCID 58828609HCID 58828609, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 2-anilino-4-methoxybenzamide (150 mg) in 5 mL dichloroethane was added pivaloyl chloride (0.229 mL), and the reaction was heated at reflux for 7 h. The reaction was cooled and partially concentrated, then diluted with ethyl ether, and the resulting precipitate was isolated by filtration to give 180 mg of a solid product. This material was dissolved in CH2Cl2 and washed with 10% sodium carbonate. The organic solution was dried (Na2SO4) and concentrated to give the titled compound.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 7 h
  3. temperatureThe reaction was cooled
  4. concentrationpartially concentrated
  5. additiondiluted with ethyl ether
  6. customthe resulting precipitate was isolated by filtration

Sources & evidence

ORD record
ord-7a39f88c949c44c1b3a41b83e57327ae
Source dataset
uspto-grants-2011_03
Patent number
US07906521B2

Reaction notes

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