Bromine → HCID 59558628, compound

HRID 1175178Notes

Reaction equation

HRID 1175178 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:14]2[N:23]=[CH:22][C:21]3[CH2:20][CH2:19][CH2:18][C:17](=[O:24])[C:16]=3[N:15]=2)[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.[Br:25]Br.C([O-])(O)=O.[Na+]>C(O)(=O)C>[Br:25][CH:18]1[C:17](=[O:24])[C:16]2[N:15]=[C:14]([C:4]3[CH:5]=[CH:6][C:7]([N:8]4[CH2:13][CH2:12][O:11][CH2:10][CH2:9]4)=[C:2]([Cl:1])[CH:3]=3)[N:23]=[CH:22][C:21]=2[CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 59558387HCID 59558387, compound

Product 1

HCID 59558628HCID 59558628, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-(3-Chloro-4-morpholin-4-yl-phenyl)-6,7-dihydro-5H-quinazolin-8-one (328 mg, 0.95 mmol) is dissolved in acetic acid (7 ml) and HBrconc. (7 ml). Bromine in HBrconc. (0.95 ml 1N solution) is added at room temperature. After stirring for one hour the mixture is poured onto ice, neutralized with NaHCO3 and the product is extracted with ethyl acetate. 1H-NMR (400 MHz; DMSO-d6): 9.10 (s, 1H), 8.43 (s, 1H), 8.28 (d, 1H), 7.30 (d, 1H), 5.21(dd, 1H), 3.76 (brs, 4H), 3.09 (brs, 4H), 3.00-2.40 (m, 4H); LC-MS (m/z, ES+): 422 (MH+), Retention time: 3.05 mins (LC-MS method 2)

Workup

  1. additionis poured onto ice
  2. extractionthe product is extracted with ethyl acetate

Sources & evidence

ORD record
ord-9226b67f0e014036a56cdc5bf581957b
Source dataset
uspto-grants-2010_11
Patent number
US07838674B2

Reaction notes

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