Sodium Iodide → HCID 19087831, compound

HRID 1464340Notes

Reaction equation

HRID 1464340 reaction equation
[CH2:1]([C:5]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]3[N:32]([CH2:33][O:34][CH3:35])[N:31]=[N:30][N:29]=3)=[CH:18][CH:17]=2)[C:13](=[O:36])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:37][CH2:38][CH2:39]Cl)[CH:11]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4].[I-].[Na+].[C:43]([O-:46])(=[O:45])[CH3:44].[Na+]>CN(C=O)C>[C:43]([O:46][CH2:39][CH2:38][O:37][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[N:6]=[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])[N:14]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]3[N:32]([CH2:33][O:34][CH3:35])[N:31]=[N:30][N:29]=3)=[CH:18][CH:17]=1)[C:13]2=[O:36])(=[O:45])[CH3:44]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 517045Sodium AcetateHCID 19087818HCID 19087818, compound

Product 1

HCID 19087831HCID 19087831, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-butyl-6-(2-chloroethyloxy)-3-[[2'-(N-methoxymethyltetrazol-5-yl)biphenyl-4-yl]methyl]-4(3H)-quinazolinone (0.59 g), sodium iodide (0.16 g) and sodium acetate (0.87 g) in DMF (15 ml) was stirred at 80° C. for 3 days. The reaction mixture was concentrated to dryness and the residue was extracted with ethyl acetate. The extract was washed with water, dried and concentrated to dryness. The residue was purified by column chromatography on silica gel to give a colorless oil (0.42 g, 68%).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-883757bb346f4e5cbe7844b8dda38d19
Source dataset
uspto-grants-1994_04
Patent number
US05304565

Reaction notes

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