Dichloromethane → HCID 86597721, compound

HRID 547837Notes

Reaction equation

HRID 547837 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([N:8]([CH3:24])[C:9](=[O:23])[C:10]([C:13]2[CH:18]=[C:17]([O:19]C)[CH:16]=[C:15]([O:21]C)[CH:14]=2)([CH3:12])[CH3:11])=[C:4]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH3:31])[CH:3]=1.C(Cl)Cl>O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([N:8]([CH3:24])[C:9](=[O:23])[C:10]([C:13]2[CH:18]=[C:17]([OH:19])[CH:16]=[C:15]([OH:21])[CH:14]=2)([CH3:11])[CH3:12])=[C:4]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH3:31])[CH:3]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 86597722HCID 86597722, compound

Product 1

HCID 86597721HCID 86597721, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2.8 g (6.4 mmol) N-(6-chloro-4-o-tolyl-pyridin-3-yl)-2-(3,5-dimethoxy-phenyl)-N-methyl-isobutyramide in 70 ml CH2Cl2 19 ml (19 mmol) BBr3 (1 M in CH2Cl2) were added at 0° C. The reaction mixture was allowed to reach ambient temperature and stirred for 15 h After addition of 50 ml water the mixture was extracted with three portions of dichloromethane. The combined organic extracts were dried (Na2SO4), filtered and evaporated. The residue was purified by flash-chromatography (SiO2, CH2Cl2/methanol) to give 2.5 g (95%) of the title compound as a white foam.

Workup

  1. customto reach ambient temperature
  2. extractionwas extracted with three portions of dichloromethane
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash-chromatography (SiO2, CH2Cl2/methanol)

Sources & evidence

ORD record
ord-0875a2b4a9e74d89b69bdf3bbff8c4a0
Source dataset
uspto-grants-2011_05
Patent number
US07939533B2

Reaction notes

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