Sulfuric Acid → HCID 12852077, compound

HRID 1156364Notes

Reaction equation

HRID 1156364 reaction equation
[O:1]=[C:2]1[N:11]([CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([C:20]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=3[NH:29]C=O)=[O:21])[CH2:16][CH2:15]2)[C:10](=[O:32])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.S(=O)(=O)(O)O.[OH-].[Na+]>C(O)C>[NH2:29][C:23]1[CH:24]=[C:25]([F:28])[CH:26]=[CH:27][C:22]=1[C:20]([CH:17]1[CH2:18][CH2:19][N:14]([CH2:13][CH2:12][N:11]2[C:10](=[O:32])[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[NH:3][C:2]2=[O:1])[CH2:15][CH2:16]1)=[O:21]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 20278957HCID 20278957, compound

Product 1

HCID 12852077HCID 12852077, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.3 parts of N-[2-[1-[2-(1,4-dihydro-2,4-dioxo-3(2H)-quinazolinyl)ethyl]-4-piperidinylcarbonyl]-5-fluorophenyl]formamide, 33 parts of concentrated sulfuric acid and 144 parts of ethanol is stirred and refluxed for 1 hour. The reaction mixture is poured onto crushed ice and alkalized with a dilute sodium hydroxide solution. The precipitated product is filtered off and crystallized from 4-methyl-2-pentanone, yielding 0.4 parts of 3-[2-[4-(2-amino-4-fluorobenzoyl)-1-piperidinyl]ethyl]-2,4(1H,3H)-quinazolinedione; mp. 269.5° C.

Workup

  1. temperaturerefluxed for 1 hour
  2. additionThe reaction mixture is poured
  3. customonto crushed ice
  4. filtrationThe precipitated product is filtered off
  5. customcrystallized from 4-methyl-2-pentanone

Sources & evidence

ORD record
ord-2a5a9baee4d84fe2a1ba2e779ef7f2b1
Source dataset
uspto-grants-1982_06
Patent number
US04335127

Reaction notes

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