Ammonium Chloride → N-[3-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-3-(2H-tetrazol-5-yl)-benzamide

HRID 2244034Notes

Reaction equation

HRID 2244034 reaction equation
[C:1]([C:4]1[CH:28]=[CH:27][C:7]([O:8][CH2:9][C:10]2[CH:11]=[C:12]([NH:16][C:17](=[O:26])[C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]#[N:25])[CH:19]=3)[CH:13]=[CH:14][CH:15]=2)=[C:6]([CH2:29][CH2:30][CH3:31])[C:5]=1[OH:32])(=[O:3])[CH3:2].[N-:33]=[N+:34]=[N-:35].[Na+].[Cl-].[NH4+]>CN(C)C=O.O>[C:1]([C:4]1[CH:28]=[CH:27][C:7]([O:8][CH2:9][C:10]2[CH:11]=[C:12]([NH:16][C:17](=[O:26])[C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]4[N:33]=[N:34][NH:35][N:25]=4)[CH:19]=3)[CH:13]=[CH:14][CH:15]=2)=[C:6]([CH2:29][CH2:30][CH3:31])[C:5]=1[OH:32])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 68431147N-[3-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-3-cyano-benzamide

Product 1

HCID 11719776N-[3-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-3-(2H-tetrazol-5-yl)-benzamideYield 33%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Heat a mixture of N-[3-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-3-cyano-benzamide (876 mg, 2.04 mmol), sodium azide (1.32 g, 20.4 mmol), and ammonium chloride (1.09 g, 20.4 mmol) in dimethylformamide (10 mL) at 110° C. overnight. Cool. Dilute with water (120 mL). Filter, and wash several times with water. Dry. Dissolve the residue in hot acetone (20 mL) and purify via chromatography, eluting with 1:1 hexanes:acetone with 1% acetic acid to afford the title compound as a light yellow powder (315 mg, 33%): 1H NMR (DMSO-d6) δ 0.89 (t, 3H), 1.51 (sextet, 2H), 2.50 (s, 3H), 2.63 (t, 2H), 5.29 (s, 2H), 6.74 (d, 1H), 7.21 (d, 1H), 7.42 (t, 1H), 7.71 (d, 1H), 7.74 (t, 1H), 7.78 (d, 1H), 7.98 (s, 1H), 8.15 (d, 1H), 8.24 (d, 1H), 8.62 (s, 1H), 10.55 (s, 1H), 12.85 (s, 1H); MS (APCI-neg mode) m/z (rel intensity) 470 (100).

Workup

  1. temperatureHeat
  2. temperatureCool
  3. filtrationFilter
  4. washwash several times with water
  5. customDry
  6. dissolutionDissolve the residue in hot acetone (20 mL)
  7. custompurify via chromatography
  8. washeluting with 1:1 hexanes

Sources & evidence

ORD record
ord-21b57cf688494cdc9bc6d1e2fc388f29
Source dataset
uspto-grants-2010_03
Patent number
US07678794B2

Reaction notes

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