Ammonium Chloride → HCID 178424964, compound

HRID 1722761Notes

Reaction equation

HRID 1722761 reaction equation
[Cl:1][C:2]1[CH:19]=[C:18]([C:20]#[N:21])[CH:17]=[C:16]([Cl:22])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[O:14][N:13]=[C:12]([CH3:15])[CH:11]=1.[N-:23]=[N+:24]=[N-:25].[Na+].[Cl-].[NH4+]>CN(C)C=O>[Cl:22][C:16]1[CH:17]=[C:18]([C:20]2[NH:25][N:24]=[N:23][N:21]=2)[CH:19]=[C:2]([Cl:1])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[O:14][N:13]=[C:12]([CH3:15])[CH:11]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 104723405-[5-(2,6-Dichloro-4-cyanophenoxy)pentyl]-3-methylisoxazole

Product 1

HCID 178424964HCID 178424964, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 14.7 g 5-[5-(2,6-dichloro-4-cyanophenoxy)pentyl]-3-methylisoxazole (Example 32a), 2.96 g sodium azide and 0.32 g ammonium chloride in 150 ml dimethylformamide was stirred and heated at 100° C. for 24 hrs. The reaction mixture was concentrated in vacuo, and the residue was dissolved in ethyl acetate and washed with 2N hydrochloric acid. The organic layer was dried over magnesium sulfate and concentrated in vacuo to a solid residue. The latter was recrystallized from ethyl acetate to give 10.3 g (62%) 5-{5-[2,6-dichloro-4-(1H-tetrazol-5yl)phenoxy]pentyl}-3-methylisoxazole, m.p. 122-123° C.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with 2N hydrochloric acid
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo to a solid residue
  6. customThe latter was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-28356ed439ba4039af5c9d2b1064f17e
Source dataset
uspto-grants-1989_08
Patent number
US04857539

Reaction notes

Loading…