Ammonium Chloride → HCID 178441408, compound

HRID 487683Notes

Reaction equation

HRID 487683 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[CH2:27][C:28]#[N:29])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[N-:30]=[N+:31]=[N-:32].[Na+].[Cl-].[NH4+]>CN(C)C=O>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[CH2:27][C:28]4[NH:32][N:31]=[N:30][N:29]=4)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 19092790HCID 19092790, compound

Product 1

HCID 178441408HCID 178441408, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 4-tert-butyl-2-[5-(2-cyanomethylphenylmethoxy)benzofuran-2-yl]thiazole (0.40 g), sodium azide (0.58 g) and ammonium chloride (0.66 g) in N,N-dimethylformamide (4 ml) was stirred at 110° C. for 8 hours. After being cooled, the mixture was poured into ice-water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated in reduced pressure to give a syrup. The syrup was subjected to column chromatography on silica gel and eluted with chloroform, successively with a mixture of chloroform and methanol (10:1). The fractions containing object compound were combined and concentrated under reduced pressure to give 5-{2-(2-(4-tert-butylthiazol-2-yl)benzofuran-5-yloxymethyl]phenylmethyl}-1H-tetrazole (0.21 g).

Workup

  1. temperatureAfter being cooled
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in reduced pressure
  6. customto give a syrup
  7. washeluted with chloroform, successively with a mixture of chloroform and methanol (10:1)
  8. additionThe fractions containing object compound
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d34ff6f00adf444da27bdd9895a29bed
Source dataset
uspto-grants-1994_03
Patent number
US05296495

Reaction notes

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