1,2-Dichloroethane → HCID 17197565, compound

HRID 594023Notes

Reaction equation

HRID 594023 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=O.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[F:26][C:27]([F:36])([F:35])[C:28]1[CH:29]=[C:30]([CH:32]=[CH:33][CH:34]=1)[NH2:31]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([NH:31][C:30]1[CH:32]=[CH:33][CH:34]=[C:28]([C:27]([F:26])([F:35])[F:36])[CH:29]=1)=[O:7]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 73753-(Trifluoromethyl)anilineHCID 757711-HydroxybenzotriazoleHCID 821303-Bromo-4-methylbenzoic acid

Product 1

HCID 17197565HCID 17197565, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-bromo-4-methylbenzoic acid (1.0 equiv.) in DMF (1.2M) was added EDC (1.0 equiv.) and HOBt (1.0 equiv.) followed by 3-trifluoromethylaniline (1.0 equiv.) and the reaction was stirred at ambient temperature for 48 h. The reaction mixture was partitioned between ethyl acetate and water. The separated organic layer was dried with sodium sulfate and concentrated under vacuo. The concentrated crude was purified via silica gel chromatography and eluted with 0 to 100% ethyl acetate in heptanes to give 3-bromo-4-methyl-N-(3-(trifluoromethyl)phenyl)benzamide in 83% yield. LCMS (m/z) (M+H)=358/360, Rt=1.1 min.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. dry with materialThe separated organic layer was dried with sodium sulfate
  3. concentrationconcentrated under vacuo
  4. concentrationThe concentrated crude
  5. customwas purified via silica gel chromatography
  6. washeluted with 0 to 100% ethyl acetate in heptanes

Sources & evidence

ORD record
ord-2ebe0e3d74d349c0a47da77fab327599
Source dataset
uspto-grants-2016_01
Patent number
US09242969B2

Reaction notes

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