Ammonium Chloride → HCID 178439700, compound

HRID 1285394Notes

Reaction equation

HRID 1285394 reaction equation
[C:1]([C:4]1[CH:23]=[CH:22][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][C:14]=2[Cl:21])=[C:6]([CH2:24][CH2:25][CH3:26])[C:5]=1[OH:27])(=[O:3])[CH3:2].[Cl-].[NH4+].[N-:30]=[N+:31]=[N-:32].[Na+]>CN(C)C=O>[C:1]([C:4]1[CH:23]=[CH:22][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[NH:32][N:31]=[N:30][N:20]=3)=[CH:15][C:14]=2[Cl:21])=[C:6]([CH2:24][CH2:25][CH3:26])[C:5]=1[OH:27])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 13338859HCID 13338859, compound

Product 1

HCID 178439700HCID 178439700, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1-(4-acetyl-3-hydroxy-2-n-propylphenoxy)-3-(2-chloro-4-cyanophenoxy)propane (776 mg), ammonium chloride (700 mg), sodium azide (700 mg) and dimethylformamide (2 ml) was heated at 120° C. for 1 hour. After the inorganic salt was filtered off, the filtrate was concentrated under reduced pressure. The residue was acidified with 1N-HCl and the resultant precipitate was recovered by filtration. Recrystallized from methanol gave 659 mg of 1-(4-acetyl-3-hydroxy-2-n-propylphenoxy)-3-[2-chloro-4-(tetrazol-5-yl)phenoxy]propane as white microcrystals. m.p. 214°-216° C.

Workup

  1. filtrationAfter the inorganic salt was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. filtrationthe resultant precipitate was recovered by filtration
  4. customRecrystallized from methanol

Sources & evidence

ORD record
ord-43af95e16db54da8a1f031b2d5c9c50e
Source dataset
uspto-grants-1986_01
Patent number
US04567201

Reaction notes

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