Sodium Hydroxide → HCID 178420708, compound

HRID 2248878Notes

Reaction equation

HRID 2248878 reaction equation
[C:1]([C:3]1[O:4][C:5]2[CH:11]=[C:10]([CH2:12][O:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][C:22]4[CH:31]=[CH:30][C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[N:23]=4)[CH:15]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1)#[N:2].[N-:32]=[N+:33]=[N-:34].[Na+].[Cl-].[NH4+].[OH-].[Na+]>CN(C=O)C>[N:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:30]=[CH:31][C:22]=1[CH2:21][O:20][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[O:13][CH2:12][C:10]1[CH:9]=[CH:8][C:6]2[N:7]=[C:3]([C:1]3[NH:34][N:33]=[N:32][N:2]=3)[O:4][C:5]=2[CH:11]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 14995282HCID 14995282, compound

Product 1

HCID 178420708HCID 178420708, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A solution-suspension of 2-cyano-6-[3-(2-quinolinylmethyloxy)phenoxymethyl]benzoxazole (660 mg, 1.62 mmol), sodium azide (316.3 mg, 4.86 mmol) and ammonium chloride (260.2 mg, 4.86 mmol) in DMF (11 ml) is heated to 110° C. for 5 hours and stirred at room temperature for 12 hours. The mixture is poured over ice-water and the pH adjusted to 10 with 1N NaOH. The aqueous mixture is washed with ether and the pH adjusted to 4 with 1N HCl. The precipitated solid is filtered and washed successively with water, ethanol and methylene chloride. Recrystallization from ethanol-DMF affords 5-(6-(3-(2-quinolinylmethyloxy)phenoxymethyl)benzoxazol-2-yl)tetrazole (M.P. 223-225° C. dec.).

Workup

  1. washThe aqueous mixture is washed with ether
  2. filtrationThe precipitated solid is filtered
  3. washwashed successively with water, ethanol and methylene chloride
  4. customRecrystallization from ethanol-DMF

Sources & evidence

ORD record
ord-c29321bcdeac43eb92df3881dea0808a
Source dataset
uspto-grants-1991_08
Patent number
US05041453

Reaction notes

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