1,2-Dichloroethane → HCID 58713642, compound

HRID 475515Notes

Reaction equation

HRID 475515 reaction equation
[O:1]=[C:2]1[CH2:22][C:5]2[C:6]([C:19]([OH:21])=[O:20])=[N:7][N:8]([S:9]([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=3)(=[O:11])=[O:10])[C:4]=2[CH2:3]1.O[N:24]1[C:28](=[O:29])[CH2:27][CH2:26][C:25]1=[O:30].C(Cl)CCl>C(Cl)Cl>[O:30]=[C:25]1[CH2:26][CH2:27][C:28](=[O:29])[N:24]1[O:20][C:19]([C:6]1[C:5]2[CH2:22][C:2](=[O:1])[CH2:3][C:4]=2[N:8]([S:9]([C:12]2[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=2)(=[O:11])=[O:10])[N:7]=1)=[O:21]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 80170N-HydroxysuccinimideHCID 23135151HCID 23135151, compound

Product 1

HCID 58713642HCID 58713642, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the intermediate from step C above, (320 mg, 1.0 mmol) in CH2Cl2(20 mL) was added N-hydroxy succinimide (230 mg, 2.0 mmol) followed by EDC (384 mg, 2.0 mmol). After stirring at room temperature for 18 hours, the reaction mixture was concentrated in vacuo. The residue was diluted with ethyl acetate (20 mL), washed with saturated NaHCO3, solution and brine. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated in vacuo. A yellow solid was obtained.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additionThe residue was diluted with ethyl acetate (20 mL)
  3. washwashed with saturated NaHCO3, solution and brine
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customA yellow solid was obtained

Sources & evidence

ORD record
ord-f725e33783aa45f9b722e391d11d184d
Source dataset
uspto-grants-2014_01
Patent number
US08637555B2

Reaction notes

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