Ammonium Chloride → HCID 178428375, compound

HRID 2305961Notes

Reaction equation

HRID 2305961 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[O:7][C:8]1[C:13]([CH3:14])=[CH:12][C:11]([NH:15][C:16]#[N:17])=[CH:10][C:9]=1[CH3:18])([CH3:3])[CH3:2].[N-:24]=[N+:25]=[N-:26].[Na+].[Cl-].[NH4+]>>[CH:1]([C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[O:7][C:8]1[C:13]([CH3:14])=[CH:12][C:11]([NH:15][C:16]2[NH:26][N:25]=[N:24][N:17]=2)=[CH:10][C:9]=1[CH3:18])([CH3:3])[CH3:2].[CH3:18][C:9]1[CH:10]=[C:11]([NH:15][C:16]2[NH:26][N:25]=[N:24][N:17]=2)[CH:12]=[C:13]([CH3:14])[C:8]=1[O:7][C:6]1[CH:19]=[CH:20][C:21]([OH:22])=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:5]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 18433440HCID 18433440, compound

Product 2

HCID 178428375HCID 178428375, compoundHCID 178492471HCID 178492471, compound

Conditions

Temperature
165 °C

Procedure

[4-(3-Isopropyl-4-methoxy-phenoxy)-3,5-dimethyl-phenyl]-(1H-tetrazol-5-yl)-amine was prepared from 4-(3-isopropyl-4-methoxy-phenoxy)-3,5-dimethyl-phenyl-cyanamide according to a procedure analogous to that described in EXAMPLE 1, Step C. Sodium azide (1.2 equiv) and ammonium chloride (10.0 equiv) were used, and the reaction was heated to 165° C. for 5 hours. After the reaction had been acidified, the mixture was extracted with ethyl acetate (3×10 ml). The combined organic extracts were washed with 1N HCl (3×50 ml) and brine (1×50 ml). The organic phase was dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified by preparative TLC (methanol:water:dichloromethane 10:0.5:89.5) to afford the title product of Step C. MS (APCI+) Calc.: 353.4, Found: 354.1 (M+1).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×10 ml)
  2. washThe combined organic extracts were washed with 1N HCl (3×50 ml) and brine (1×50 ml)
  3. dry with materialThe organic phase was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by preparative TLC (methanol:water:dichloromethane 10:0.5:89.5)

Sources & evidence

ORD record
ord-f53e8336fc344713860091e0059c0c68
Source dataset
uspto-grants-2002_08
Patent number
US06441015B2

Reaction notes

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