Ammonium Chloride → HCID 178478471, compound

HRID 224406Notes

Reaction equation

HRID 224406 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH:10]([C:12]([Cl:15])([Cl:14])[Cl:13])[O:9][CH:8]([C:16]([Cl:19])([Cl:18])Cl)[C:7]=2[CH:20]=1)#[N:2].[Cl-].[NH4+].[N-:23]=[N+:24]=[N-:25].[Na+]>CN(C)C=O>[Cl:18][C:16]([Cl:19])=[C:8]1[C:7]2[CH:20]=[C:3]([C:1]3[NH:25][N:24]=[N:23][N:2]=3)[CH:4]=[CH:5][C:6]=2[O:11][CH:10]([C:12]([Cl:13])([Cl:14])[Cl:15])[O:9]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 233329632,4-Bis(trichloromethyl)-2H,4H-1,3-benzodioxine-6-carbonitrile

Product 1

HCID 178478471HCID 178478471, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-cyano-2,4-bis(trichloromethyl)benzo[1,3]dioxin (1.98 g.), ammonium chloride (0.33 g.) and sodium azide in anhydrous dimethylformamide was warmed on the steam bath for 16 hours. The reaction mixture was cooled, poured onto ice and kept for 16 hours. The amorphous white product was filtered off, triturated with acetic acid, and crystallised from chloroform to give 4-dichloromethylene-6-(tetrazol-5-yl)-2-trichloromethylbenzo[1,3]dioxin, m.p. 222° C.

Workup

  1. temperaturewas warmed on the steam bath for 16 hours
  2. temperatureThe reaction mixture was cooled
  3. additionpoured onto ice
  4. filtrationThe amorphous white product was filtered off
  5. customtriturated with acetic acid
  6. customcrystallised from chloroform

Sources & evidence

ORD record
ord-03e5f3dcdc014a4f9a1b26ebd567e47f
Source dataset
uspto-grants-1980_11
Patent number
US04232032

Reaction notes

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