Sodium Iodide → HCID 18476664, compound

HRID 651326Notes

Reaction equation

HRID 651326 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([CH3:17])[C:7]1=[O:18].ClCCCCN1C(=O)C2C(=CC=CC=2)N(C)C1=O.[I-:37].[Na+]>C(C(C)=O)C>[I:37][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([CH3:17])[C:7]1=[O:18]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 18476649HCID 18476649, compoundHCID 18476654HCID 18476654, compound

Product 1

HCID 18476664HCID 18476664, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A solution of the title A compounds, 3-(4-bromobutyl)-1,2,3,4-tetrahydro-1-methyl-2,4-dioxoquinazoline and 3-(4-chlorobutyl)-1,2,3,4-tetrahydro-1-methyl-2,4-dioxoquinazoline (1:1 mixture; 2.35 g, 8.13 mmol) in 30 mL of methyl ethyl ketone is treated with sodium iodide (2.64 g, 17.62 mmol) at RT. The reaction is heated at reflux for 16 h, then cooled and the solvent is evaporated under reduced pressure. The residue is partitioned between 200 mL of ethyl acetate and 5 mL of water. The organic solution is washed with 10 mL of 1% aqueous sodium sulfite and 10 mL of brine, dried over anhydrous MgSO4, and concentrated to give 3.10 g (100%) of 3-(4-iodobutyl)-1,2,3,4-tetrahydro-1-methyl-2,4-dioxoquinazoline as a white solid: m.p. 105-107° C.; NMR (CDCl3) 1.75-1.95 (m, 4H), 3.22 (t, 2H, J=6.8), 3.59 (s, 3H), 4.11 (t, 2H, J=7.1), 7.17-7.28 (m, 2H), 7.67 (dt, 1H, J=1.6, 7.9), 8.21 (dd, 1H, J=1.5, 7.9); IR 1702, 1658; ESI-MS 359 (M++1).

Workup

  1. temperatureThe reaction is heated
  2. temperatureat reflux for 16 h
  3. temperaturecooled
  4. customthe solvent is evaporated under reduced pressure
  5. customThe residue is partitioned between 200 mL of ethyl acetate and 5 mL of water
  6. washThe organic solution is washed with 10 mL of 1% aqueous sodium sulfite and 10 mL of brine
  7. dry with materialdried over anhydrous MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f53b2ccb46124f679121419fbaf7d8db
Source dataset
uspto-grants-2001_08
Patent number
US06277987B1

Reaction notes

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