1,2-Dichloroethane → HCID 54297219, compound

HRID 1683053Notes

Reaction equation

HRID 1683053 reaction equation
C([N:8]1[CH2:26][CH2:25][C:11]2([N:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:14](=[O:23])[NH:13][C:12]2=[O:24])[CH2:10][CH2:9]1)C1C=CC=CC=1.ClCCCl.ClC(OC(Cl)C)=O>CO>[F:22][C:19]1[CH:20]=[CH:21][C:16]([N:15]2[C:11]3([CH2:10][CH2:9][NH:8][CH2:26][CH2:25]3)[C:12](=[O:24])[NH:13][C:14]2=[O:23])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 5213051-Chloroethyl chloroformateHCID 53759290HCID 53759290, compound

Product 1

HCID 54297219HCID 54297219, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Combine 8-benzyl-1-(4-fluoro-phenyl)-1,3,8-triaza-spiro[4.5]decane-2,4-dione (10 mmol) and 1,2-dichloroethane (70 mL). Cool using an ice bath. Add in dropwise fashion, 1-chloroethyl chloroformate (48.6 mmol). Warm to ambient temperature and maintain for 1 h. Extract using saturated NaHCO3 (120 mL). Extract the aqueous phase using dichloromethane (120 mL). Combine the organic layers, extract with saturated NaCl, dry over Na2SO4, filter, and concentrate in vacuo to obtain a residue. Add anhydrous methanol (70 mL) and heat at reflux for 1 h. Concentrate in vacuo to obtain a residue and purify to obtain the title compound.

Workup

  1. temperatureCool
  2. temperaturemaintain for 1 h
  3. extractionExtract
  4. extractionExtract the aqueous phase
  5. extractionCombine the organic layers, extract with saturated NaCl
  6. dry with materialdry over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate in vacuo
  9. customto obtain a residue
  10. temperatureat reflux for 1 h
  11. concentrationConcentrate in vacuo
  12. customto obtain a residue
  13. custompurify

Sources & evidence

ORD record
ord-5cb933a4d7fd476ea85a5958d8dbbc79
Source dataset
uspto-grants-1997_06
Patent number
US05635510

Reaction notes

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