Potassium Iodide → HCID 54236221, compound

HRID 437661Notes

Reaction equation

HRID 437661 reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5]([C:7]1[O:8][CH:9]=[CH:10][CH:11]=1)=[O:6].[C:12]1([N:18]2[C:22]3([CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[C:21](=[O:28])[NH:20][CH2:19]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[I-].[K+]>CN(C)C=O>[O:28]=[C:21]1[C:22]2([CH2:23][CH2:24][N:25]([CH2:2][CH2:3][NH:4][C:5]([C:7]3[O:8][CH:9]=[CH:10][CH:11]=3)=[O:6])[CH2:26][CH2:27]2)[N:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:19][NH:20]1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 705561-Phenyl-1,3,8-triazaspiro(4.5)decan-4-oneHCID 182358N-(2-Chloroethyl)-2-furamide

Product 1

HCID 54236221HCID 54236221, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A member of 6.9 parts of N-(2-chloroethyl)-2-furancarboxamide, 9.2 parts of 1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one, 6.6 parts of potassium iodide and 135 parts of N,N-dimethylformamide is stirred first for 3 hours at reflux and further overnight at room temperature. The reaction mixture is evaporated and the residue is taken up in water. The whole is alkalized and the product is extracted with 4-methyl-2-pentanone. The extract is dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (96:4 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The solid residue is crystallized from 2-propanone. The product is filtered off and dried, yielding 1.9 parts of N-[2-(4-oxo-1-phenyl-1,3,8-triazaspiro [4,5]dec-8-yl)ethyl]-2-furancarboxamide; mp. 196.3° C.

Workup

  1. customThe reaction mixture is evaporated
  2. extractionthe product is extracted with 4-methyl-2-pentanone
  3. customThe extract is dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is purified by column-chromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol (96:4 by volume) as eluent
  8. customThe pure fractions are collected
  9. customthe eluent is evaporated
  10. customThe solid residue is crystallized from 2-propanone
  11. filtrationThe product is filtered off
  12. customdried

Sources & evidence

ORD record
ord-4ab325a9b662424abdb147dbcfead2b4
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

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