Thionyl Chloride → methyl 3-(8-cyano-6-iodo-4-oxoquinazolin-3(4H)-yl)-4-methylbenzoate

HRID 641967Notes

Reaction equation

HRID 641967 reaction equation
[NH2:1][C:2]([C:4]1[CH:5]=[C:6]([I:26])[CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][N:10]([C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][C:23]=1[CH3:24])[C:17]([O:19][CH3:20])=[O:18])[C:9]2=[O:25])=O.S(Cl)(Cl)=O>CN(C=O)C>[C:2]([C:4]1[CH:5]=[C:6]([I:26])[CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][N:10]([C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][C:23]=1[CH3:24])[C:17]([O:19][CH3:20])=[O:18])[C:9]2=[O:25])#[N:1]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 68603905methyl 3-[8-(aminocarbonyl)-6-iodo-4-oxoquinazolin-3(4H)-yl]-4-methylbenzoate

Product 1

HCID 68603006methyl 3-(8-cyano-6-iodo-4-oxoquinazolin-3(4H)-yl)-4-methylbenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of methyl 3-[8-(aminocarbonyl)-6-iodo-4-oxoquinazolin-3(4H)-yl]-4-methylbenzoate in DMF (15 ml) was added thionyl chloride (1.79 ml). The reaction mixture was stirred at room temperature for 30 minutes and ice-water added. The resultant mixture was extracted with methylene chloride (×2) and the combined organic layers washed with water, saturated NaHCO3 solution, dried (magnesium sulphate) and concentrated to yield methyl 3-(8-cyano-6-iodo-4-oxoquinazolin-3(4H)-yl)-4-methylbenzoate as a white solid (2.04 g); NMR Spectrum: (DMSOd6) 2.19 (s, 3H), 3.88 (s, 3H), 7.61 (d, 1H), 8.03 (m, 2H), 8.53 (s, 1H), 8.67 (d, 1H), 8.74 (d, 1H); Mass Spectrum: M+H+ 446.

Workup

  1. extractionThe resultant mixture was extracted with methylene chloride (×2)
  2. washthe combined organic layers washed with water, saturated NaHCO3 solution
  3. dry with materialdried (magnesium sulphate)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d7b0523822ae47fd96129651cf820183
Source dataset
uspto-grants-2010_04
Patent number
US07696215B2

Reaction notes

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