Water → HCID 178420172, compound

HRID 622769Notes

Reaction equation

HRID 622769 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[N:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH2:19][C:20]#[N:21])[CH:16]=[CH:17][CH:18]=1.[N-:22]=[N+:23]=[N-:24].[Na+].[Cl-].[NH4+].O>CN(C)C=O.C(OCC)(=O)C>[NH:22]1[C:20]([CH2:19][C:15]2[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=2)[O:12][CH2:11][C:2]2[N:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=2)=[N:21][N:24]=[N:23]1

Participants

7

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 143023903-(2-Quinazolinylmethoxy)benzenacetonitrile

Product 1

HCID 178420172HCID 178420172, compoundYield 54.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
135 °C

Procedure

To a solution of 6.3 g (0.023 mol) of 3-(2-quinazolinylmethoxy)benzenacetonitrile in 150 ml of dimethylformamide are added 7.5 g (0.115 mol) of sodium azide and 6.2 g (0.115 mol) of ammonium chloride, and the slurry is heated to 135° C. for 72 hours. The slurry is poured into 500 ml of water/500 ml of ethyl acetate, and the layers are separated. The aqueous phase is twice extracted with 250 ml of ethyl acetate, and the combined ethyl acetate solution is twice washed with 500 ml of water, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain 4 g of crystals, m.p. 129°-131° C. Recrystallization from ethanol gives 2.5 g (34%) of crystals, m.p. 129°-131° C., MS(CI) 319 (M+H).

Workup

  1. customthe layers are separated
  2. extractionThe aqueous phase is twice extracted with 250 ml of ethyl acetate
  3. washthe combined ethyl acetate solution is twice washed with 500 ml of water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fe6617dd6d6a4fdb93b10ae711414126
Source dataset
uspto-grants-1988_09
Patent number
US04772703

Reaction notes

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