N,N-Dimethylbenzamide → HCID 22555997, compound

HRID 985154Notes

Reaction equation

HRID 985154 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 71.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Combined under Ar 108 (3.00 g, 13.2 mmol) and tetrahydrofuran. Cooled in an IPA/dry ice bath. Added dropwise n-butyllithium solution (2.5M in hexanes, 11.1 mL, 27.8 mmol). Stirred 0.5 h with cooling then warmed over 0.5 h to −15° C. Recooled using IPA/dry ice and added a tetrahydrofuran solution of N,N-dimethylbenzamide (2.38 g, 15.8 mmol). Warmed to room temperature and quenched with water. Removed solvent in vacuo; added sat. sodium bicarbonate and extracted with ethyl acetate (3×). Dried combined organic portions with sodium sulfate (anh.), filtered, removed solvent in vacuo. A solid resulted which was triturated with ether to give 109 as a white solid (3.11 g, 9.39 mmol, 71.2%).

Workup

  1. temperatureCooled in an IPA/dry ice bath
  2. temperaturewith cooling
  3. temperaturethen warmed over 0.5 h to −15° C
  4. customquenched with water
  5. extractionadded sat. sodium bicarbonate and extracted with ethyl acetate (3×)
  6. customDried
  7. filtrationfiltered
  8. customremoved solvent in vacuo
  9. customA solid resulted which
  10. customwas triturated with ether

Sources & evidence

ORD record
ord-91d7519564634c9c896223d1c41f9fcc
Source dataset
uspto-grants-2005_03
Patent number
US06870055B2

Reaction notes

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