Phosphorus oxychloride → HCID 89781950, compound

HRID 1056392Notes

Reaction equation

HRID 1056392 reaction equation
[Br: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][C:14]([F:17])([F:16])[F:15])[C:7]2=[O:18].P(Cl)(Cl)([Cl:21])=O.CCN(C(C)C)C(C)C>>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([Cl:21])[N:8]([CH2:13][C:14]([F:17])([F:16])[F:15])[C:7]2=[O:18]

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 89783877HCID 89783877, compound

Product 1

HCID 89781950HCID 89781950, compoundYield 76.5%

Procedure

8-Bromo-2-chloro-3-(2,2,2-trifluoroethyl)quinazolin-4(3H)-one (501c) as an off-white solid (1.22 g, 76%) was prepared according to the procedures described for 720 using 8-bromo-3-(2,2,2-trifluoroethyl)quinazoline-2,4(1H,3H)-dione (1.51 g, 4.67 mmol, 501b), phosphorus oxychloride (2.1 mL, 23.37 mmol, Sigma Aldrich), and DIEA (3.3 mL, 18.70 mmol, Sigma Aldrich). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.23 (1H, dd, J=7.82, 1.37 Hz) 8.16 (1H, dd, J=7.82, 1.37 Hz) 7.53 (1H, t, J=7.92 Hz) 5.11 (2H, q, J=8.74 Hz). m/z (ESI, +ve) 342.8/344.8 (M+H)+.

Sources & evidence

ORD record
ord-5f65cd21582c49eabec646c1852012f0
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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