1,2-Dichloroethane → HCID 57483944, compound

HRID 919331Notes

Reaction equation

HRID 919331 reaction equation
[CH2:1]([CH:8]([C:12]([NH:14][O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:13])[C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[N:24]1[C:28](=[O:29])[CH2:27][CH2:26][C:25]1=[O:30].C(Cl)CCl>CC#N>[O:30]=[C:25]1[CH2:26][CH2:27][C:28](=[O:29])[N:24]1[O:10][C:9](=[O:11])[CH:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:12]([NH:14][O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:13]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 80170N-HydroxysuccinimideHCID 13242795HCID 13242795, compound

Product 1

HCID 57483944HCID 57483944, compoundYield 117.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Intermediate (12a) (0.5 g, 1.7 mmol) was added to N-hydroxysuccinimide (290 mg, 2.6 mmol) and EDC (320 mg, 1.7 mmol) and dissolved in MeCN (6 mL). The mixture was stirred overnight at room temperature and then partitioned between EtOAc and 10% aqueous citric acid. The organic layer was separated, washed with saturated aqueous NaCl, dried over MgSO4, filtered and concentrated to provide intermediate (12b) as a foam (0.8 g, 2 mmol).

Workup

  1. custompartitioned between EtOAc and 10% aqueous citric acid
  2. customThe organic layer was separated
  3. washwashed with saturated aqueous NaCl
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-71ab5da6259d40c2b4e04d085610e510
Source dataset
uspto-grants-2016_03
Patent number
US09273008B2

Reaction notes

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