Ammonium Chloride → 1-(4-fluorobenzyl)-4-(4-methyl-5-(2H-tetrazol-5-yl)thiazol-2-yl)-1H-1,2,4-triazol-5(4H)-one

HRID 555018Notes

Reaction equation

HRID 555018 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[C:11](=[O:12])[N:10]([C:13]3[S:14][C:15]([C:19]#[N:20])=[C:16]([CH3:18])[N:17]=3)[CH:9]=[N:8]2)=[CH:4][CH:3]=1.[N-:23]=[N+:24]=[N-:25].[Na+].[Cl-].[NH4+]>CN(C)C=O>[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[C:11](=[O:12])[N:10]([C:13]3[S:14][C:15]([C:19]4[N:23]=[N:24][NH:25][N:20]=4)=[C:16]([CH3:18])[N:17]=3)[CH:9]=[N:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 579198502-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carbonitrile

Product 1

HCID 579198311-(4-fluorobenzyl)-4-(4-methyl-5-(2H-tetrazol-5-yl)thiazol-2-yl)-1H-1,2,4-triazol-5(4H)-oneYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carbonitrile (0.10 g, 0.31 mmol), sodium azide (0.08 g, 1.57 mmol) and ammonium chloride (0.07 g, 1.57 mmol) in anhydrous N,N-dimethylformamide (5.0 mL) was heated at 80° C. for 16 h. The reaction was quenched with the addition of water (2.0 mL) and the solvents were removed in vacuo. The residue was dissolved with ethyl acetate (10 mL), washed with water (2×2 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The residue was crystallized from methanol and ether to afford the title compound as a colourless solid (0.08 g, 72%): mp 136-139° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.80 (s, 1H), 7.42-7.37 (m, 2H), 7.23-7.17 (m, 2H), 6.17 (br, 1H), 5.02 (s, 2H), 2.75 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 161.6 (d), 158.7, 151.8, 149.7, 148.6, 132.1 (d), 132.0, 129.9 (d), 115.4 (d), 113.6, 47.7, 16.7; MS (ES−) m/z 356.9 (M−1).

Workup

  1. customThe reaction was quenched with the addition of water (2.0 mL)
  2. customthe solvents were removed in vacuo
  3. dissolutionThe residue was dissolved with ethyl acetate (10 mL)
  4. washwashed with water (2×2 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo to dryness
  8. customThe residue was crystallized from methanol and ether

Sources & evidence

ORD record
ord-21baab8e45104b1bb23e48d5405ae339
Source dataset
uspto-grants-2011_11
Patent number
US08049016B2

Reaction notes

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