1,2-Dichloroethane → HCID 67697967, compound

HRID 1683044Notes

Reaction equation

HRID 1683044 reaction equation
C([N:8]1[CH2:25][CH2:24][C:11]2([N:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH:14]=[N:13][C:12]2=[O:23])[CH2:10][CH2:9]1)C1C=CC=CC=1.[Cl:26]CCCl.ClC(OC(Cl)C)=O>CO>[ClH:26].[F:22][C:19]1[CH:20]=[CH:21][C:16]([N:15]2[C:11]3([CH2:10][CH2:9][NH:8][CH2:25][CH2:24]3)[C:12](=[O:23])[N:13]=[CH:14]2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 5213051-Chloroethyl chloroformateHCID 45789390HCID 45789390, compound

Product 1

HCID 67697967HCID 67697967, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Combine 8-benzyl-1-(4-fluoro-phenyl)-1,3,8-triazaspiro[4.5]dec-2-en-4-one (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 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 in vacuo
  12. customto obtain a residue
  13. custompurify

Sources & evidence

ORD record
ord-8242631a7698496d8d6d62138be7ca64
Source dataset
uspto-grants-1997_06
Patent number
US05635510

Reaction notes

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