Water → HCID 22052252, compound

HRID 1831609Notes

Reaction equation

HRID 1831609 reaction equation
[CH2:1]([C:3]1[N:12]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[C:11](=[O:20])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH3:21])[N:4]=1)[CH3:2].C([O-])(=O)C.[Na+].[Br:27]Br.O>C(O)(=O)C>[Br:27][CH:1]([C:3]1[N:12]([C:13]2[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=2)[C:11](=[O:20])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH3:21])[N:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 517045Sodium AcetateHCID 22052254HCID 22052254, compound

Product 1

HCID 22052252HCID 22052252, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a mixture of 1.969 g 2-ethyl-3-(4-fluoro-phenyl)-5-methyl-3H-quinazolin-4-one (IX) (6.974 mmol, 1.000 equiv) and 0.687 g sodium acetate (8.37 mmol, 1.20 equiv) in 28 mL glacial acetic acid at 40° C. (external temperature, oil bath) was added a solution of 0.372 mL bromine (7.32 mmol, 1.05 equiv) dissolved in 5 mL glacial acetic acid dropwise by addition funnel over 30 min. After 2 h the reaction solution was poured into 250 mL water. The resulting mixture was stirred vigorously at room temperature for 1 h, after which time the precipitate was collected by vacuum filtration, rinsing with warm (ca. 40° C.) water (3×50 mL). The solid was dried in vacuo over phosphorous pentoxide overnight, affording 2.19 g of a white solid. m.p. decomposes upon heating. 1H NMR (CDCl3) δ 2.04 (d, 3H, J=6.8 Hz), 2.82 (s, 3H), 4.51 (q, 1H, J=6.8 Hz), 7.15 (ddd, 1H, J1=2.4 Hz, J2=4.4 Hz, J3=8.4 Hz), 7.23 (dd, 1H, J1=2.8 Hz, J2=10.8 Hz), 7.25–7.31 (m, 2H), 7.56 (ddd, J1=2.8 Hz, J2=4.8 Hz, J3=8.8 Hz), 7.64 (2×d, 2×1H, J=5.2 Hz) ppm. MS (ESI+) 361.1 [MH]+.

Workup

  1. filtrationafter which time the precipitate was collected by vacuum filtration
  2. washrinsing
  3. temperaturewith warm (ca. 40° C.) water (3×50 mL)
  4. dry with materialThe solid was dried in vacuo over phosphorous pentoxide overnight

Sources & evidence

ORD record
ord-e3b4119a6c3945419c3528d6a9349454
Source dataset
uspto-grants-2006_06
Patent number
US07067662B2

Reaction notes

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