N,N-Dimethylbenzamide → HCID 22555997, compound

HRID 2358290Notes

Reaction equation

HRID 2358290 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:8])=[CH:5][CH:4]=1.C([Li])CCC.CC(O)C.C(=O)=O.CN(C)[C:32](=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>O1CCCC1>[OH:39][C:32]1([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:5]2[C:6](=[CH:16][CH:17]=[C:3]([O:2][CH3:1])[CH:4]=2)[C:7](=[O:8])[N:9]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 11916N,N-DimethylbenzamideHCID 3460374-methoxy-N-phenylbenzamideHCID 86586944Isopropanol carbon dioxideHCID 178418339Butyllithium

Product 1

HCID 22555997HCID 22555997, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

While cooling in a dry ice/isopropanol bath, to a solution of 1 (3.00 g, 13.2 mmol) in tetrahydrofuran at −78° C. was added dropwise n-butyllithium (2.5M in hexanes, 11.1 mL, 27.8 mmol). After stirring for 0.5 h the reaction mixture was warmed over 0.5 h to −15° C. It was recooled in the IPA/dry ice bath then a tetrahydrofuran solution of N,N-dimethylbenzamide (2.38 g, 15.8 mmol) was added. The reaction mixture was warmed to room temperature and quenched with water. The solvent was removed in vacuo. Sat. sodium bicarbonate was added and the mixture extracted with ethyl acetate (3×). The combined organic portions were dried with sodium sulfate (anh.), filtered, and concentrated. A solid resulted. It was triturated with ether to give 2 as a white solid (3.11 g, 71%)

Workup

  1. temperaturewas warmed over 0.5 h to −15° C
  2. customquenched with water
  3. customThe solvent was removed in vacuo
  4. additionSat. sodium bicarbonate was added
  5. extractionthe mixture extracted with ethyl acetate (3×)
  6. dry with materialThe combined organic portions were dried with sodium sulfate (anh.)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customA solid resulted
  10. customIt was triturated with ether

Sources & evidence

ORD record
ord-001db45eff8c4e7f9f70ad90cbd5b21a
Source dataset
uspto-grants-2010_07
Patent number
US07763614B2

Reaction notes

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