Phosphorus oxychloride → 2-chloro-8-iodo-3-(3-(methylsulfonyl)propyl)quinazolin-4(3H)-one

HRID 1056416Notes

Reaction equation

HRID 1056416 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=O)[N:8]([CH2:13][CH2:14][CH2:15][S:16]([CH3:19])(=[O:18])=[O:17])[C:7]2=[O:20].CCN(C(C)C)C(C)C.P(Cl)(Cl)([Cl:32])=O>>[Cl:32][C:9]1[N:8]([CH2:13][CH2:14][CH2:15][S:16]([CH3:19])(=[O:18])=[O:17])[C:7](=[O:20])[C:6]2[C:11](=[C:2]([I:1])[CH:3]=[CH:4][CH:5]=2)[N:10]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 897837608-iodo-3-(3-(methylsulfonyl)propyl)quinazoline-2,4(1H,3H)-dione

Product 1

HCID 897819212-chloro-8-iodo-3-(3-(methylsulfonyl)propyl)quinazolin-4(3H)-one

Conditions

Temperature
120 °C

Procedure

A pressure vessel was charged with 8-iodo-3-(3-(methylsulfonyl)propyl)-quinazoline-2,4(1H,3H)-dione (1.09 g, 2.67 mmol), DIEA (1.858 mL, 10.68 mmol) and phosphorus oxychloride (1.222 mL, 13.35 mmol). The tube was sealed and heated in an oil bath at 120° C. for 3 h, then cooled to RT. The solvent was removed in vacuo and the residue was poured into ice/water (50 mL) and 1 M NaOH was added until pH 10. The suspension was filtered and the solid was dried to give the crude product. MS (ESI, pos. ion) m/z: 426.8 (M+1).

Workup

  1. customThe tube was sealed
  2. temperaturecooled to RT
  3. customThe solvent was removed in vacuo
  4. additionthe residue was poured into ice/water (50 mL) and 1 M NaOH
  5. additionwas added until pH 10
  6. filtrationThe suspension was filtered
  7. customthe solid was dried

Sources & evidence

ORD record
ord-8f0d8623e77a4b1eaa96a9df4c86ef2e
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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