1,2-Dichloroethane → Benzamide

HRID 479737Notes

Reaction equation

HRID 479737 reaction equation
ON1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2N=N1.C(Cl)CCl.C(OCC)(=O)C.C[N:22](C)[CH:23]=[O:24]>>[C:23]([NH2:22])(=[O:24])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 757711-Hydroxybenzotriazole

Product 1

HCID 2331Benzamide

Procedure

To a solution of 175 mg (1.15 mmol) of 3-hydroxy-2-1methylbenzoic acid and 203 mg (1.5 mmol) of N-hydroxybenzotriazole in 6 mL of anhydrous N,N-dimethylformamide at 0° C., was added 220 mg (1.15 mmol) of EDC. After 20 minutes of activation at 0° C. and 1 hour at room temperature, 392 mg (1.0 mmol) of 2R-hydroxy-3-[(2-methylpropyl)(4-aminophenyl)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 590 mg of crude material. This was chromatographed on silica gel using 50-80% ethyl acetate/methylene chloride as eluent to afford 255 mg of pure benzamide, N-[2R-hydroxy-3-[[(4-aminophenyl)sulfonyl](2-methylpropyl)amino)-1S-(phenylmethyl)propyl]-3-hydroxy-2-methyl, m/e=526(M+H).

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 590 mg of crude material
  7. customThis was chromatographed on silica gel using 50-80% ethyl acetate/methylene chloride as eluent

Sources & evidence

ORD record
ord-29616a98c0014db6adfee3ff1d4c044a
Source dataset
uspto-grants-2003_11
Patent number
US06646010B2

Reaction notes

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