Ammonium Chloride → HCID 178441997, compound

HRID 493508Notes

Reaction equation

HRID 493508 reaction equation
[CH2:1]([C:5]1[O:6][C:7]2[CH:32]=[CH:31][CH:30]=[CH:29][C:8]=2[C:9]=1[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]#[N:28])=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)=[O:11])[CH2:2][CH2:3][CH3:4].[N-:33]=[N+:34]=[N-:35].[Na+].[Cl-].[NH4+]>C(OCC)(=O)C>[CH2:1]([C:5]1[O:6][C:7]2[CH:32]=[CH:31][CH:30]=[CH:29][C:8]=2[C:9]=1[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]3[NH:35][N:34]=[N:33][N:28]=3)=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)=[O:11])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 68858475HCID 68858475, compound

Product 1

HCID 178441997HCID 178441997, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-butyl-N-(4′-cyanomethoxy[1,1′-biphenyl]-4-yl)-1-benzofuran-3-carboxamide (400 mg, 0.942 mmol), prepared in the previous step, sodium azide (184 mg, 2.83 mmol) and ammonium chloride (151 mg, 2.83 mmol) was stirred under nitrogen at 100+ C. for 5.5 h. The reaction was diluted with ethyl acetate and extracted with 1 N NaOH. The aqueous layer was separated, extracted one additional time with ethyl acetate and acidified by the addition of 1 N HCl. The solid that formed was collected by filtration and dried under reduced pressure to give the title compound (257 mg, 59%) as a white solid, mp 210-212° C.; MS (APCI) m/z 468 ([M+H]+. Elemental Analysis for C27H25N5O3+0.06 H2O: Calc'd: C, 69.20; H, 5.40; N, 14.94; Found: C, 68.83; H, 5.29; N, 14.98

Workup

  1. extractionextracted with 1 N NaOH
  2. customThe aqueous layer was separated
  3. extractionextracted one additional time with ethyl acetate
  4. additionacidified by the addition of 1 N HCl
  5. customThe solid that formed
  6. filtrationwas collected by filtration
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-358cc1176fa14c9db9abe72f0c68c502
Source dataset
uspto-grants-2009_05
Patent number
US07534894B2

Reaction notes

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