Sodium Iodide → HCID 21484919, compound

HRID 1414715Notes

Reaction equation

HRID 1414715 reaction equation
Cl.[OH:2][C:3]1[N:8]=[CH:7][CH:6]=[CH:5][N:4]=1.C([O-])([O-])=O.[Na+].[Na+].[Na+].[I-].Cl[CH2:18][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=1>CO>[CH:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:27]=[CH:28][C:19]=1[CH2:18][N:4]1[CH:5]=[CH:6][CH:7]=[N:8][C:3]1=[O:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 756322-(Chloromethyl)naphthaleneHCID 178479648HCID 178479648, compound

Product 1

HCID 21484919HCID 21484919, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 14.6 g (0.11 mole) portion of 2-hydroxypyrimidine hydrochloride in 700 ml of methanol was treated with 23.3 g (0.22 mole) of Na2CO3, 7.5 g (0.05 mole) of NaI and 20.0 g (0.11 mole) of 2-(chloromethyl) naphthalene. The reaction mixture was refluxed for 18 hrs and concentrated to dryness under reduced pressure. The solid was taken up in 200 ml of H2O and extracted with 300 ml of CHCl3. The chloroform extract was washed with 100 ml of H2O, dried over MgSO4 for 2 hrs and filtered. The filtrate was concentrated under reduced pressure to give 24 g (92%) of a cream solid, m.p. 136°-145°.

Workup

  1. temperatureThe reaction mixture was refluxed for 18 hrs
  2. concentrationconcentrated to dryness under reduced pressure
  3. extractionextracted with 300 ml of CHCl3
  4. extractionThe chloroform extract
  5. washwas washed with 100 ml of H2O
  6. dry with materialdried over MgSO4 for 2 hrs
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6d1b95318a044ed5aa336920aaaa3426
Source dataset
uspto-grants-1977_01
Patent number
US04002626

Reaction notes

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