1,2-Dichloroethane → Benzamide

HRID 724233Notes

Reaction equation

HRID 724233 reaction equation
O[C:2]1[C:3](C)=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](O)=[O:6].O[N:13]1C2C=CC=CC=2N=N1.C(Cl)CCl.C(OCC)(=O)C>CN(C)C=O>[C:5]([NH2:13])(=[O:6])[C:4]1[CH:8]=[CH:9][CH:10]=[CH:2][CH:3]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 8857Ethyl AcetateHCID 757711-HydroxybenzotriazoleHCID 2520233-Hydroxy-2-methylbenzoic Acid

Product 1

HCID 2331BenzamideYield 275.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 131 mg (0.86 mmol) of 3-hydroxy-2-methylbenzoic acid and 305 mg (0.75mmol) of N-hydroxybenzotriazole in 4 mL of anhydrous N,N-dimethylformamide at 0° C., was added 165 mg (0.86 mmol) of EDC. After 20 minutes of activation at 0° C. and 1 hour at room temperature, 305 mg (0.75 mmol) of 2R-hydroxy-3-[(2-methylpropyl) (4-methoxyphenyl)sulfonyl]amino-1S-(phenylmethyl)propylamine was added. After 15 hours at room temperature, ethyl acetate was added, washed with 5% citric acid, saturated sodium bicarbonate, brine, dried, filtered and concentrated to afford 460 mg of crude material. This was chromatographed on silica gel using 0–35% ethyl acetate/methylene chloride as eluent to afford 250 mg of pure benzamide, N-[2R-hydroxy-3-([(4-methoxyphenyl)sulfonyl](2-methylpropyl)amino]-1S-(phenylmethyl)propyl]-3-hydroxy-2-methyl, m/e=547 (M+Li).

Workup

  1. waitAfter 15 hours at room temperature
  2. washwashed with 5% citric acid, saturated sodium bicarbonate, brine
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford 460 mg of crude material
  7. customThis was chromatographed on silica gel using 0–35% ethyl acetate/methylene chloride as eluent

Sources & evidence

ORD record
ord-cdc1dfd15a434023914696ea39d4d613
Source dataset
uspto-grants-2006_11
Patent number
US07141609B2

Reaction notes

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