Sodium Hydroxide → HCID 178422380, compound

HRID 2248907Notes

Reaction equation

HRID 2248907 reaction equation
[C:1]([C:3]1[S:7][C:6]2[CH:8]=[CH:9][C:10]([O:12][CH2:13][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:11][C:5]=2[C:4]=1[CH3:32])#[N:2].[N-:33]=[N+:34]=[N-:35].[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)[CH2:13][O:12][C:10]1[CH:9]=[CH:8][C:6]2[S:7][C:3]([C:1]3[NH:35][N:34]=[N:33][N:2]=3)=[C:4]([CH3:32])[C:5]=2[CH:11]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 14995292HCID 14995292, compound

Product 1

HCID 178422380HCID 178422380, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution-suspension of 2-cyano-5-[3-(2-quinolinylmethyloxy)benzyloxy]-3-methylbenzo(b)thiophene (300 mg, 0.69 mmol), sodium azide (134 mg, 2.1 mmol) and ammonium chloride (110.3 mg, 2.1 mmol) in DMF (3 ml) is heated to 80° C. for 16 hours. The reaction mixture is cooled to room temperature and poured over ice-water. The pH is adjusted to 10 (1N NaOH) and the aqueous layer washed with ether and then acidified to pH 3. The precipitated solid is filtered and washed successively with water, ethanol and methylene chloride and dried to afford 5-(5-[3-(2quinolinylmethyloxy)benzyloxy]-3-methylbenzo(b)thiophen -2-yl)tetrazole (M.P. 195-196° C. (dec)).

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. washthe aqueous layer washed with ether
  3. filtrationThe precipitated solid is filtered
  4. washwashed successively with water, ethanol and methylene chloride
  5. customdried

Sources & evidence

ORD record
ord-1fbdc3412dbc4ac4b81bc417a42e8594
Source dataset
uspto-grants-1991_08
Patent number
US05041453

Reaction notes

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