Water → HCID 21958885, compound

HRID 412015Notes

Reaction equation

HRID 412015 reaction equation
[CH2:1]([C:4]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:12](=[O:21])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)[CH2:2][CH3:3].C([O-])(=O)C.[Na+].[Br:27]Br.O>C(O)(=O)C>[Br:27][CH:1]([C:4]1[N:13]([CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:12](=[O:21])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 517045Sodium AcetateHCID 3335159HCID 3335159, compound

Product 1

HCID 21958885HCID 21958885, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a three-neck 250 mL round-bottom flask equipped with a thermometer, dropping funnel, and efficient magnetic stir bar was added compound 4 (27.8 g, 0.10 mole), anhydrous sodium acetate (10.0 g) and glacial acetic acid (130 mL). Bromine (16.0 g, 0.10 mole) dissolved in acetic acid (10 mL) was added dropwise to the above solution at 40° C. for 1-2 h. After addition was complete, the mixture was poured into water (1500 mL) and stirred for 1-2 h at room temperature. The precipitated product, 2-(1′-bromopropyl)-3-benzylquinazolin-4-one (5) was isolated by filtration, washed with warm water to remove traces of acetic acid, and rinsed with a small amount of isopropanol. Drying yielded compound 5 (33.0 g, 92%).

Workup

  1. customTo a three-neck 250 mL round-bottom flask equipped with a thermometer
  2. additionwas added dropwise to the above solution at 40° C. for 1-2 h
  3. additionAfter addition

Sources & evidence

ORD record
ord-20d38dffc8db41fea100ff4754edc263
Source dataset
uspto-grants-2003_05
Patent number
US06562831B1

Reaction notes

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