Pyridine → HCID 22449610, compound

HRID 1464272Notes

Reaction equation

HRID 1464272 reaction equation
O[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[NH:8][C:7]1=[O:17].S(Cl)([Cl:20])=O.N1C=CC=CC=1>O1CCCC1>[Cl:20][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[NH:8][C:7]1=[O:17]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 19087700HCID 19087700, compound

Product 1

HCID 22449610HCID 22449610, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-(4-hydroxybutyl)-2,4(1H,3H)-quinazolinedione 290 mg), thionyl chloride (0.54 ml), and pyridine (98 mg) in tetrahydrofuran (10 ml) was refluxed for 2 hours. After evaporation of the solvents, the residue was dissolved in chloroform, washed in turn with water, saturated sodium bicarbonate and brine, dried over magnesium sulfate, and evaporated. Crude material was crystallized from ethyl ether-isopropyl ether to give 1-(4-chlorobutyl)-2,4(1H,3H)-quinazolinedione (226 mg) as a powder.

Workup

  1. temperaturewas refluxed for 2 hours
  2. customAfter evaporation of the solvents
  3. dissolutionthe residue was dissolved in chloroform
  4. washwashed in turn with water, saturated sodium bicarbonate and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customCrude material was crystallized from ethyl ether-isopropyl ether

Sources & evidence

ORD record
ord-86c975f0c8aa417ab8f12e819cef6353
Source dataset
uspto-grants-1994_04
Patent number
US05304560

Reaction notes

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