1,2-Dichloroethane → HCID 16124851, compound

HRID 1945393Notes

Reaction equation

HRID 1945393 reaction equation
[N+]([C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][C:10]([OH:12])=O)=[CH:6][CH:5]=1)([O-])=O.[NH2:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19]([NH2:21])=[O:20].C1C=C[C:28]2N(O)N=N[C:29]=2[CH:30]=1.[CH3:35]CN(C(C)C)C(C)C.C(Cl)CCl>CN(C=O)C.CO>[C:29]([C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]([NH:15][C:16]2[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=2)[C:19]([NH2:21])=[O:20])=[O:12])=[CH:13][CH:14]=1)([CH3:28])([CH3:30])[CH3:35]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 16453-AminobenzamideHCID 15720(4-Nitrophenoxy)acetic acidHCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine

Product 1

HCID 16124851HCID 16124851, compoundYield 82.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (4-nitrophenoxy)-acetic acid (100 mg, 0.5 mmol), 3-amino benzamide (103.5 mg, 0.76 mmol), HOBt (102.81 mg, 0.76 mmol) and DIPEA (98.34 mg, 0.76 mmol) in DMF (2 ml) was added EDC (145.86 mg, 0.76 mmol) at room temperature and the resulting mixture was stirred until reaction completion as indicated by TLC. Reaction mixture was poured onto ice cold water, diluted with a mixture of MeOH:MC (10%), separated organic layer and sequentially washed with aqueous sodium bicarbonate, brine and water, and dried over anhydrous MgSO4. The solvent was filtered and evaporated under reduced pressure to afford a crude solid, which was purified flash chromatography on silica gel (MeOH:MC=1:9-2:8) to afford of 3-[2-(4-tert-butyl-phenoxy)acetylamino]-benzamide as a colorless solid (135 mg, 81% yield).

Workup

  1. customReaction mixture
  2. additionwas poured onto ice cold water
  3. customMC (10%), separated organic layer
  4. washsequentially washed with aqueous sodium bicarbonate, brine and water
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationThe solvent was filtered
  7. customevaporated under reduced pressure
  8. customto afford a crude solid, which
  9. customwas purified flash chromatography on silica gel (MeOH:MC=1:9-2:8)

Sources & evidence

ORD record
ord-85b01301f4b34013b01e69391c318b14
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

Loading…