Hydrogen Peroxide → HCID 13851175, compound

HRID 978444Notes

Reaction equation

HRID 978444 reaction equation
[F:1][C:2]1[CH:32]=[CH:31][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]3[C:25](=[O:26])[C:24]4[C:19](=[CH:20][C:21]([N+:27]([O-:29])=[O:28])=[CH:22][CH:23]=4)[NH:18][C:17]3=S)[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[OH-:33].[K+].O.OO>C(O)C.C(O)(=O)C>[F:1][C:2]1[CH:32]=[CH:31][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]3[C:25](=[O:26])[C:24]4[C:19](=[CH:20][C:21]([N+:27]([O-:29])=[O:28])=[CH:22][CH:23]=4)[NH:18][C:17]3=[O:33])[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 962Water2×HCID 14797Potassium HydroxideHCID 20202883HCID 20202883, compound

Product 1

HCID 13851175HCID 13851175, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

To a stirred mixture of 7 parts of 3-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-2,3-dihydro-7-nitro-2-thioxo-4(1H)-quinazolinone, 120 parts of a solution of potassium hydroxide in ethanol 5% and 10 parts of water were added dropwise 100 parts of a hydrogen peroxide solution 3% during a 10 minutes period. Upon completion, stirring was continued for 2.50 hours at room temperature. Then there were added 100 parts of water and the whole was neutralized with acetic acid. The precipitated product was filtered off and crystallized from a mixture of N,N-dimethylacetamide and water, yielding 4.8 parts of 3-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-7-nitro-2,4(1H,3H)-quinazolinedione; mp. 238.1°-240.1° C. (23).

Workup

  1. filtrationThe precipitated product was filtered off
  2. customcrystallized from a mixture of N,N-dimethylacetamide and water

Sources & evidence

ORD record
ord-8b0d199bdc6c4e8cb6087a7021c68fd3
Source dataset
uspto-grants-1987_05
Patent number
US04665075

Reaction notes

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