Cyanogen Bromide → 3-(2-Amino-3-propyl-3,4-dihydro-quinazolin-6-yloxy)-benzonitrile

HRID 390220Notes

Reaction equation

HRID 390220 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)[C:10]#[N:11])=[CH:4][C:3]=1[CH2:17][NH:18][CH2:19][CH2:20][CH3:21].[N:22]#[C:23]Br>C(O)C>[NH2:22][C:23]1[N:18]([CH2:19][CH2:20][CH3:21])[CH2:17][C:3]2[C:2](=[CH:16][CH:15]=[C:5]([O:6][C:7]3[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=3)[C:10]#[N:11])[CH:4]=2)[N:1]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 586251143-(4-Amino-3-propylaminomethyl-phenoxy)-benzonitrile

Product 1

HCID 586250633-(2-Amino-3-propyl-3,4-dihydro-quinazolin-6-yloxy)-benzonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-(4-amino-3-propylaminomethyl-phenoxy)-benzonitrile (0.032 mol) in ethanol (400 mL) was stirred at room temperature, and cyanogen bromide (0.038 mol) was added, and then the reaction mixture was stirred and refluxed for 2 hours. After cooling, the precipitate was filtered off, washed with diisopropyl ether and dried to yield crude product as a solid.

Workup

  1. stirringthe reaction mixture was stirred
  2. temperaturerefluxed for 2 hours
  3. temperatureAfter cooling
  4. filtrationthe precipitate was filtered off
  5. washwashed with diisopropyl ether
  6. customdried
  7. customto yield crude product as a solid

Sources & evidence

ORD record
ord-58fed401931749de9b0f5ca92aefa48a
Source dataset
uspto-grants-2013_02
Patent number
US08383637B2

Reaction notes

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