4H-1,3-Benzodioxin-6-amine, 2,4-bis(trichloromethyl)- → 2,4-Bis(trichloromethyl)-2H,4H-1,3-benzodioxine-6-diazonium chloride

HRID 224400Notes

Reaction equation

HRID 224400 reaction equation
[N:1]([O-])=O.[Na+].[NH2:5][C:6]1[CH:7]=[CH:8][C:9]2[O:14][CH:13]([C:15]([Cl:18])([Cl:17])[Cl:16])[O:12][CH:11]([C:19]([Cl:22])([Cl:21])[Cl:20])[C:10]=2[CH:23]=1>O.Cl>[Cl-:16].[Cl:18][C:15]([Cl:16])([Cl:17])[CH:13]1[O:12][CH:11]([C:19]([Cl:22])([Cl:21])[Cl:20])[C:10]2[CH:23]=[C:6]([N+:5]#[N:1])[CH:7]=[CH:8][C:9]=2[O:14]1

Participants

5

Reactant 2

HCID 44090764H-1,3-Benzodioxin-6-amine, 2,4-bis(trichloromethyl)-HCID 23668193Sodium Nitrite

Product 1

HCID 233329382,4-Bis(trichloromethyl)-2H,4H-1,3-benzodioxine-6-diazonium chloride

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

A solution of sodium nitrite (1.96 g.) in water (30 ml.) was added to a stirred suspension of 6-amino-2,4-bis(trichloromethyl)benzo[1,3]dioxin (10 g.) in a mixture of hydrochloric acid (40 ml.) and water (180 ml.), cooled to 0°-5° C. The suspension was stirred for 1 hour at 0°-5° C., the mixture was filtered, and the solid product was washed with water, dried and crystallised from water to give 2,4-bis(trichloromethyl)benzo[1,3]dioxin-6-diazonium chloride, m.p. 140°-142° C.

Workup

  1. temperaturecooled to 0°-5° C
  2. filtrationthe mixture was filtered
  3. washthe solid product was washed with water
  4. customdried
  5. customcrystallised from water

Sources & evidence

ORD record
ord-daa894456d104da18eeec80f4ea99ea5
Source dataset
uspto-grants-1980_11
Patent number
US04232032

Reaction notes

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