Carbon Tetrachloride → 4(1H)-Quinazolinone

HRID 1798762Notes

Reaction equation

HRID 1798762 reaction equation
[CH:1]1[CH:6]=[C:5]2[C:7]([NH:9][C:10]([NH:12][C:4]2=[CH:3][CH:2]=1)=O)=[O:8].C(Cl)(Cl)(Cl)Cl.CCN(C(C)C)C(C)C.P([O-])(OCC1C=CC=CC=1)OCC1C=CC=CC=1>CC#N.CN(C1C=CN=CC=1)C>[CH:1]1[CH:2]=[CH:3][C:4]2[N:12]=[CH:10][NH:9][C:7](=[O:8])[C:5]=2[CH:6]=1

Participants

7

Reactant 4

HCID 5943Carbon TetrachlorideHCID 64048QuinazolinedioneHCID 81531DiisopropylethylamineHCID 21904359Dibenzylphosphite

Product 1

HCID 1354087534(1H)-QuinazolinoneYield 185.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent2×

Procedure

The quinazoline 1 (0.2 g, 0.62 mmol) was dissolved in CH3CN (5 mL). After cooling to −10° C. (ice/NaCl), CCl4, DIEA and DMAP were added. After stirring for 10 min, a solution of dibenzyl phosphite in CH3CN (2 mL) was slowly added over 10 min. Stirring was continued at −10° C. for 2 h, then at RT for 24 h. Quenched by addition of 0.5 M K2HPO4, diluted with water (15 mL), extracted with DCM (30 mL), dried, concentrated, purified by flash chromatography (100% DCM) to obtain 2 (168 mg, 47% yield) as a colorless oil. LC/MS (10-99%) M/Z 586.0 retention time 2.54 min.

Workup

  1. additionwere added
  2. stirringStirring
  3. waitwas continued at −10° C. for 2 h
  4. waitat RT for 24 h
  5. customQuenched by addition of 0.5 M K2HPO4
  6. additiondiluted with water (15 mL)
  7. extractionextracted with DCM (30 mL)
  8. customdried
  9. concentrationconcentrated
  10. custompurified by flash chromatography (100% DCM)

Sources & evidence

ORD record
ord-2f29c48c9a0b4461ac7e471ac32c04d3
Source dataset
uspto-grants-2013_01
Patent number
US08343980B2

Reaction notes

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