Sodium Iodide → HCID 178482462, compound

HRID 652588Notes

Reaction equation

HRID 652588 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:18][CH3:19])[C:5]([O:16][CH3:17])=[C:6]2[C:11]=1[N:10]=[C:9]([O:12]C)[N:8]=[C:7]2[NH:14][CH3:15].[I-].[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([O:18][CH3:19])[C:5]([O:16][CH3:17])=[C:6]2[C:11]=1[N:10]=[C:9]([OH:12])[N:8]=[C:7]2[NH:14][CH3:15]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 13914737HCID 13914737, compound

Product 1

HCID 178482462HCID 178482462, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 8-chloro-2,5,6-trimethoxy-4-methylaminoquinazoline (1.80 g, 0.0054 moles), sodium iodide (0.989 g, 0.0066 moles) and glacial acetic acid (50 ml) was refluxed for 8 minutes. The glacial acetic acid was removed in vacuo and the residue was diluted with water (100 ml). After extracting the aqueous solution with dichloromethane (2×25 ml) the combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. Recrystallization of the residue from ethyl acetate-isopropanol afforded the product (0.530 g), mp 219°-221° C.

Workup

  1. customThe glacial acetic acid was removed in vacuo
  2. additionthe residue was diluted with water (100 ml)
  3. extractionAfter extracting the aqueous solution with dichloromethane (2×25 ml) the combined organic extracts
  4. dry with materialwere dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customRecrystallization of the residue from ethyl acetate-isopropanol

Sources & evidence

ORD record
ord-9e253a5e896642a7b903a776dca90b55
Source dataset
uspto-grants-1987_06
Patent number
US04672116

Reaction notes

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