Methanol → 4-fluoro-2-nitro-N-[2-(4-oxo-1-phenyl-1,3,8-triazaspiro-[4,5]dec-8-yl)ethyl]benzamide

HRID 437626Notes

Reaction equation

HRID 437626 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([N:8]2[CH2:10][CH2:9]2)=[O:7])=[C:4]([N+:13]([O-:15])=[O:14])[CH:3]=1.[C:16]1([N:22]2[C:26]3([CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)[C:25](=[O:32])[NH:24][CH2:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CO>C1C=CC=CC=1>[F:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([NH:8][CH2:10][CH2:9][N:29]2[CH2:28][CH2:27][C:26]3([N:22]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH2:23][NH:24][C:25]3=[O:32])[CH2:31][CH2:30]2)=[O:7])=[C:4]([N+:13]([O-:15])=[O:14])[CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 705561-Phenyl-1,3,8-triazaspiro(4.5)decan-4-oneHCID 214288531-(4-Fluoro-2-nitrobenzoyl)aziridine

Product 1

HCID 214288434-fluoro-2-nitro-N-[2-(4-oxo-1-phenyl-1,3,8-triazaspiro-[4,5]dec-8-yl)ethyl]benzamide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 15 parts of 1-(4-fluoro-2-nitrobenzoyl)-aziridine, 12 parts of 1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one, 8.8 parts of methanol and 56 parts of benzene is stirred first for 1.50 hours at reflux and further overnight at room temperature. The reaction mixture is evaporated. The residue is dissolved in trichloromethane and the solution is washed with water. Then there are added 8 parts of methanol and silica gel and the whole is stirred for 10 minutes. The silica gel is filtered off and the filtrate is evaporated. The residue is stirred in 2,2'-oxybispropane. The product is filtered off and crystallized from 4-methyl-2-pentanone. It is filtered off and dried, yielding 13 parts of 4-fluoro-2-nitro-N-[2-(4-oxo-1-phenyl-1,3,8-triazaspiro-[4,5]dec-8-yl)ethyl]benzamide; mp. 160° C.

Workup

  1. customThe reaction mixture is evaporated
  2. dissolutionThe residue is dissolved in trichloromethane
  3. washthe solution is washed with water
  4. additionThen there are added 8 parts of methanol and silica gel
  5. stirringthe whole is stirred for 10 minutes
  6. filtrationThe silica gel is filtered off
  7. customthe filtrate is evaporated
  8. stirringThe residue is stirred in 2,2'-oxybispropane
  9. filtrationThe product is filtered off
  10. customcrystallized from 4-methyl-2-pentanone
  11. filtrationIt is filtered off
  12. customdried

Sources & evidence

ORD record
ord-45c967df8eeb40c08c61fb3d7319e0b2
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

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