Sodium Hydroxide → HCID 178517465, compound

HRID 1191306Notes

Reaction equation

HRID 1191306 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[C:18]3[C:13](=[C:14]4[CH:22]=[CH:21][CH:20]=[CH:19][C:15]4=[CH:16][CH:17]=3)[NH:12][C:11](=[O:23])[N:10]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2].C([Sn]([N:37]=[N+:38]=[N-:39])(CCCC)CCCC)CCC.[OH-].[Na+]>CN(C=O)C>[NH:37]1[C:1]([C:3]2[CH:4]=[C:5]([C:9]3[C:18]4[C:13](=[C:14]5[CH:22]=[CH:21][CH:20]=[CH:19][C:15]5=[CH:16][CH:17]=4)[NH:12][C:11](=[O:23])[N:10]=3)[CH:6]=[CH:7][CH:8]=2)=[N:2][N:39]=[N:38]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 4984872Tributyltin azideHCID 566506744-(3-Cyanophenyl)-1H-benzo[h]quinazolin-2-one

Product 1

HCID 178517465HCID 178517465, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 4-(3-cyanophenyl)-1H-benzo[h]quinazolin-2-one (112 mg, 0.377 mmol) in DMF (2 mL) was added tri-n-butyltin azide (312 μL, 1.13 mmol), and stirred at 110° C. for 18 hours. After cooled to room temperature, the reaction mixture was poured into 1M sodium hydroxide, and washed with ethyl acetate. After aqueous layer was neutralized with 1M hydrochloric acid, the precipitated solid was collected by filtration, washed with methanol, and with water. The obtained crystal was dried to give the titled compound as a yellow crystal (70 mg, yield 55%).

Workup

  1. temperatureAfter cooled to room temperature
  2. washwashed with ethyl acetate
  3. filtrationthe precipitated solid was collected by filtration
  4. washwashed with methanol
  5. customThe obtained crystal was dried

Sources & evidence

ORD record
ord-d89b142ed1a74580aae3f75a5b16a52b
Source dataset
uspto-grants-2014_03
Patent number
US08680110B2

Reaction notes

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