Ammonium Chloride → HCID 178441406, compound

HRID 1604655Notes

Reaction equation

HRID 1604655 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]([CH2:19][C:20]4[S:21][CH:22]=[C:23]([CH2:25][C:26]#[N:27])[N:24]=4)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[N-:28]=[N+:29]=[N-:30].[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]([CH2:19][C:20]4[S:21][CH:22]=[C:23]([CH2:25][C:26]5[NH:30][N:29]=[N:28][N:27]=5)[N:24]=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 19603707HCID 19603707, compound

Product 1

HCID 178441406HCID 178441406, compoundYield 56.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-tert-butyl-2-{5-{[4-(cyanomethyl)thiazol-2-yl]methyl}benzofuran-2-yl}thiazole (0.19 g), sodium azide (0.43 g) and ammonium chloride (0.36 g) in N,N-dimethylformamide (3 ml) was stirred at 120° C. for 3 days. 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 under reduced pressure to give a syrup. The syrup was subjected to column chromatography on silica gel and eluted with a mixture of chloroform and methanol (50:1), 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-yl]methyl}thiazol-4-ylmethyl}-1H-tetrazole (0.12 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 under reduced pressure
  6. customto give a syrup
  7. washeluted with a mixture of chloroform and methanol (50:1), 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-516730f5b4ca4fdbadf1ab87ede5d2e1
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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