Dimethylformamide → HCID 18404846, compound

HRID 469834Notes

Reaction equation

HRID 469834 reaction equation
C(Cl)(=O)C(Cl)=O.[Br:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[C:10]([CH3:17])[CH:9]=1.CN(C=O)C.[NH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>ClCCl>[Br:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[O:14])=[C:10]([CH3:17])[CH:9]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8083MorpholineHCID 65578Oxalyl chlorideHCID 995704-Bromo-2-methylbenzoic acid

Product 1

HCID 18404846HCID 18404846, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 10.6 ml (47 mmol) oxalyl chloride in 30 ml dichloromethane is added dropwise to a iced-cooled solution of 5.21 g (23.5 mmol) 4-bromo-2-methyl-benzoic acid and 0.0087 ml DMF in 100 ml CH2Cl2. After complete addition, the cooling bath is removed and stirring maintained for 2 h at RT. The solvent is evaporated to dryness and the residue is dried in vacuo and dissolved in 100 ml dichloromethane and 8.21 ml N-ethyl-diisopropylamine is added. To this solution 2.5 ml (28 mmol) morpholine is added slowly. Stirring is continued for 0.5 h, then the reaction mixture is poured on water and extracted 3× with EtOAc. The combined organic layers are washed with water and saturated NaCl solution, dried over MgSO4, filtered and the filtrate is concentrated in vacuo to afford the title compound which is used in the next step without further purification.

Workup

  1. additionAfter complete addition
  2. customthe cooling bath is removed
  3. customThe solvent is evaporated to dryness
  4. customthe residue is dried in vacuo
  5. dissolutiondissolved in 100 ml dichloromethane
  6. addition8.21 ml N-ethyl-diisopropylamine is added
  7. stirringStirring
  8. additionthe reaction mixture is poured on water
  9. extractionextracted 3× with EtOAc
  10. washThe combined organic layers are washed with water and saturated NaCl solution
  11. dry with materialdried over MgSO4
  12. filtrationfiltered
  13. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-71e3565079544e7f9b154731688b97ba
Source dataset
uspto-grants-2014_01
Patent number
US08629168B2

Reaction notes

Loading…