Triphosgene → 8-iodo-3-(3-(methylthio)propyl)quinazoline-2,4(1H,3H)-dione

HRID 1056414Notes

Reaction equation

HRID 1056414 reaction equation
[NH2:1][C:2]1[C:15]([I:16])=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][CH2:9][S:10][CH3:11])=[O:5].Cl[C:18](Cl)([O:20]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[I:16][C:15]1[CH:14]=[CH:13][CH:12]=[C:3]2[C:2]=1[NH:1][C:18](=[O:20])[N:6]([CH2:7][CH2:8][CH2:9][S:10][CH3:11])[C:4]2=[O:5]

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 897819962-amino-3-iodo-N-(3-(methylthio)propyl)benzamide

Product 1

HCID 897844618-iodo-3-(3-(methylthio)propyl)quinazoline-2,4(1H,3H)-dioneYield 319%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 100 mL round-bottomed flask was added 2-amino-3-iodo-N-(3-(methylthio)propyl)benzamide (1.25 g, 3.57 mmol) and triphosgene (0.185 mL, 1.25 mmol, Sigma Aldrich) in DCM (20 mL). The reaction was heated to reflux for 15 h, and then cooled to RT. The solvent was removed to give the crude product 1.5 g. MS (ESI, pos. ion) m/z: 376.9 (M+1).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 15 h
  3. customThe solvent was removed

Sources & evidence

ORD record
ord-aacf6d78e3d14b848e710b9d1ec88553
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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