Anisole → HCID 22647916, compound

HRID 394077Notes

Reaction equation

HRID 394077 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:18]2[C:13](=[C:14]([Br:21])[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=2)[CH2:12][N:11](CC2C=CC(OC)=CC=2)[C:10]1=[O:31].C1(OC)C=CC=CC=1>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:18]2[C:13](=[C:14]([Br:21])[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=2)[CH2:12][NH:11][C:10]1=[O:31]

Participants

4

Reactant 2

HCID 7519AnisoleHCID 22647922HCID 22647922, compound2×

Product 1

HCID 22647916HCID 22647916, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 1-(2,6-dichlorophenyl)-3-(4-methoxyphenyl)methyl-5-bromo-7-methoxy-3,4-dihydro-2(1H)-quinazolinone (30.91 g, 0.0592 mol) (INTERMEDIATE 22) and anisole (28 ml, 0.258 mol) in 350 mL trifluoroacetic acid under a nitrogen atmosphere was refluxed for 2 h. The solution was cooled to RT and concentrated. The residue was partitioned between 500 mL NaHCO3 and 500 mL EtOAc. The organic phase was washed with water (500 mL) and brine (500 mL) and concentrated. The NaHCO3 and brine phases contained a suspension of precipitated product. This material was collected by filtration and combined with the crude. The combined crude was suspended in ethyl ether, filtered and washed with ethyl ether and hexanes to give 1-(2,6-dichlorophenyl)-5-bromo-7-methoxy-3,4-dihydro-2(1H)-quinazolinone. 1H NMR(CDCl3, 500 MHz): δ 3.68 (s, 3H), 4.64 (s, 2H), 5.46 (s, 1H), 5.62 (d, 1H, J=2.3 Hz), 6.79 (d, 1H, J=2.5 Hz), 7.36 (t, 1H, J=8.1 Hz), 7.50 (d, 2H, J=8.2 Hz). MS(ES) 401 (M+1); LC 1: 3.18 min.

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between 500 mL NaHCO3 and 500 mL EtOAc
  3. washThe organic phase was washed with water (500 mL) and brine (500 mL)
  4. concentrationconcentrated
  5. additiona suspension of precipitated product
  6. filtrationThis material was collected by filtration
  7. filtrationfiltered
  8. washwashed with ethyl ether and hexanes

Sources & evidence

ORD record
ord-8c8c1cf37c9a4a9ba476b06bee0ad9d1
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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