Benzene → HCID 21428840, compound

HRID 437627Notes

Reaction equation

HRID 437627 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=1[C:6]([N:8]1[CH2:10][CH2:9]1)=[O:7])([O-:3])=[O:2].[F:15][C:16]1[CH:21]=[CH:20][C:19]([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:18][CH:17]=1.C1C=CC=CC=1.CO.[Cl:41]C(Cl)Cl>>[ClH:41].[F:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[C:26]3([CH2:27][CH2:28][N:29]([CH2:9][CH2:10][NH:8][C:6](=[O:7])[C:5]4[CH:11]=[CH:12][CH:13]=[CH:14][C:4]=4[N+:1]([O-:3])=[O:2])[CH2:30][CH2:31]3)[C:25](=[O:32])[NH:24][CH2:23]2)=[CH:18][CH:17]=1

Participants

6

Reactant 5

HCID 241BenzeneHCID 887MethanolHCID 6212ChloroformHCID 939151-(4-Fluorophenyl)-1,3,8-triazaspiro(4.5)decan-4-oneHCID 214289511-(2-Nitrobenzoyl)aziridine

Product 1

HCID 21428840HCID 21428840, compound

Procedure

A mixture of 7.6 parts of 1-(2-nitrobenzoyl)aziridine, 9.97 parts of 1-(4-fluorophenyl)-1,3,8-triazaspiro[4,5]decan-4-one, 43.2 parts of benzene and 6.4 parts of methanol is stirred and refluxed for 1.50 hours. Trichloromethane is added and the whole is washed three times with water. The undissolved precipitate is filtered off and the organic phase is dried, filtered and evaporated. The residue is converted into the hydrochloride salt in 2-propanone and 2-propanol. The salt is filtered off and crystallized from a mixture of ethanol and water. It is filtered off and dried in vacuo, yielding 2.7 parts of N-{2-[1-(4-fluorophenyl)-4-oxo1,3,8-triazaspiro[4,5]dec-8-yl]ethyl}-2-nitrobenzamide hydrochloride; m.p. 267.2° C.

Workup

  1. temperaturerefluxed for 1.50 hours
  2. washthe whole is washed three times with water
  3. filtrationThe undissolved precipitate is filtered off
  4. customthe organic phase is dried
  5. filtrationfiltered
  6. customevaporated
  7. filtrationThe salt is filtered off
  8. customcrystallized from a mixture of ethanol and water
  9. filtrationIt is filtered off
  10. customdried in vacuo

Sources & evidence

ORD record
ord-679f88cd45f44c04ae0fc31a15a726dc
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

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