1,2-Dichloroethane → Pentanediamide

HRID 2259838Notes

Reaction equation

HRID 2259838 reaction equation
[CH:1]1[CH:2]=CC2N(O)N=[N:7][C:5]=2[CH:6]=1.C(Cl)CCl.N.C(OCC)(=[O:18])C.C[N:23]([CH:25]=[O:26])C>CO.C(Cl)Cl>[C:5]([NH2:7])(=[O:18])[CH2:6][CH2:1][CH2:2][C:25]([NH2:23])=[O:26]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 222AmmoniaHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 757711-Hydroxybenzotriazole

Product 1

HCID 230227Pentanediamide

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Part B. To a solution of 92 mg (0.19 mmol) of product from part A and 38 mg (0.28 mmol) HOBT in 0.5 mL DMF at 0° C. was added 36 mg (0.19 mmol) of EDC. After 30 minutes at 0° C., 0.25 mL of conc. aqueous ammonia was added. After 1 hour at 0° C. and 16 hours at RT, ethyl acetate was added, washed with 0.2N HCl , sat'd NaHCO3, brine, dried and concentrated to afford 72 mg of crude product. This was passed through a one-inch column of basic alumina with 10% methanol/methylene chloride to afford 53 mg of desired product, m/e=491 (M+H).

Workup

  1. waitAfter 1 hour at 0° C.
  2. washwashed with 0.2N HCl
  3. customdried
  4. concentrationconcentrated
  5. customto afford 72 mg of crude product

Sources & evidence

ORD record
ord-edfc3862843c43a1af3df910e97f9a19
Source dataset
uspto-grants-1995_12
Patent number
US05475013

Reaction notes

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