1,2-Dichloroethane → HCID 58713650, compound

HRID 475505Notes

Reaction equation

HRID 475505 reaction equation
[CH2:1]([N:8]1[C:12]2[CH2:13][C:14](=[O:16])[CH2:15][C:11]=2[C:10]([C:17]([OH:19])=[O:18])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[N:21]1[C:25](=[O:26])[CH2:24][CH2:23][C:22]1=[O:27].C(Cl)CCl>C(Cl)Cl>[O:27]=[C:22]1[CH2:23][CH2:24][C:25](=[O:26])[N:21]1[O:18][C:17]([C:10]1[C:11]2[CH2:15][C:14](=[O:16])[CH2:13][C:12]=2[N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[N:9]=1)=[O:19]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 80170N-HydroxysuccinimideHCID 23135167HCID 23135167, compound

Product 1

HCID 58713650HCID 58713650, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the intermediate from step C (1.34 g, 5.25 mmol) in CH2Cl2 (50 mL) was added N-hydroxy succinimide (1.21 g, 10.5 mmol) followed by EDC (2.01 g, 10.5 mmol). After stirring at room temperature for 18 hours, the reaction mixture was concentrated in vacuo. The residue was diluted with ethyl acetate (200 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 (200 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-10c5674a07b24b0c8b285edd34f5121b
Source dataset
uspto-grants-2014_01
Patent number
US08637555B2

Reaction notes

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