1,2-Dichloroethane → HCID 910367, compound

HRID 1945390Notes

Reaction equation

HRID 1945390 reaction equation
[O:1]([CH2:8][C:9]([OH:11])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16]([NH2:18])=[O:17].C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.C(Cl)CCl>CN(C=O)C.CO>[O:1]([CH2:8][C:9]([NH:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16]([NH2:18])=[O:17])=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 16453-AminobenzamideHCID 19188Phenoxyacetic AcidHCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine

Product 1

HCID 910367HCID 910367, compoundYield 83.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of phenoxy-acetic acid (100 mg, 0.65 mmol), 3-amino benzamide (178.9 mg, 1.31 mmol), HOBt (177.7 mg, 1.31 mmol) and DIPEA (170 mg, 1.31 mmol) in DMF (6 ml) was added EDC (252 mg, 1.31 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-phenoxy-acetyl-amino)-benzamide as a colorless solid (146 mg, 82% 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-90be40f96ab24300bcf46e2a3ce8bd67
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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