Phosphorus oxychloride → 4-Chloro-2-{1-[4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-quinazoline

HRID 238224Notes

Reaction equation

HRID 238224 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:17][CH2:16][N:15]([CH:18]([C:20]3[NH:29][C:28](=O)[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:21]=3)[CH3:19])[CH2:14][CH2:13]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.P(Cl)(Cl)([Cl:33])=O>>[Cl:33][C:28]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]=[C:20]([CH:18]([N:15]2[CH2:16][CH2:17][N:12]([S:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)(=[O:11])=[O:10])[CH2:13][CH2:14]2)[CH3:19])[N:29]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1358460552-{1-[4-(4-Methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-3H-quinazolin-4-one

Product 1

HCID 599934264-Chloro-2-{1-[4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-quinazolineYield 100%

Conditions

Temperature
90 °C

Procedure

In a flask containing of 2-{1-[4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-3H-quinazolin-4-one (380.0 mg, 0.89 mmol) in phosphorus oxychloride (20 ml) was heated to 90° C. for 2 hours, then the solvent was concentrated under reduced pressure to give 4-Chloro-2-{1-[4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-quinazoline (Yield 394.2 mg, 100%) that was used directly without further purification. 1H NMR (400 MHz, CDCl-3): δ 1.93 (d, 3H, J=6.82 Hz), 3.23-3.04 (m, 3H), 3.54-3.34 (m, 1H), 3.87-3.65 (m, 4H), 3.90 (s, 3H), 4.77 (q, 1H, J=14.15, 6.82 Hz), 7.05 (d, 2H, J=8.84), 7.69 (d, 2H, J=8.84), 7.87 (t, H, J=7.84), 8.10 (t, 1H, J=8.34 Hz), 8.18 (d, 1H, 8.34 Hz), 8.35 (d, 1H, 8.34 Hz). MS m/z calc. 446.12, found (ESI); 447.4 (M+1)+. Retention time 2.67 minutes.

Workup

  1. concentrationthe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a2438411fc6e4a268b76cd103819416d
Source dataset
uspto-grants-2014_02
Patent number
US08642609B2

Reaction notes

Loading…