Ammonium Chloride → 4-(Dichloromethylidene)-2-(trichloromethyl)-2H,4H-1,3-benzodioxine-6-carboxylic acid

HRID 224405Notes

Reaction equation

HRID 224405 reaction equation
[Cl:1][C:2]([Cl:21])([Cl:20])[CH:3]1[O:8][CH:7]([C:9](Cl)([Cl:11])[Cl:10])[C:6]2[CH:13]=[C:14]([C:17]([OH:19])=[O:18])[CH:15]=[CH:16][C:5]=2[O:4]1.[Cl-].[NH4+].[N-]=[N+]=[N-].[Na+]>CS(C)=O>[Cl:11][C:9]([Cl:10])=[C:7]1[C:6]2[CH:13]=[C:14]([C:17]([OH:19])=[O:18])[CH:15]=[CH:16][C:5]=2[O:4][CH:3]([C:2]([Cl:1])([Cl:21])[Cl:20])[O:8]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 1941342,4-Bis(trichloromethyl)-2H,4H-1,3-benzodioxine-6-carboxylic acid

Product 1

HCID 1941334-(Dichloromethylidene)-2-(trichloromethyl)-2H,4H-1,3-benzodioxine-6-carboxylic acid

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 2,4-bis(trichloromethyl)benzo[1,3]dioxin-6-carboxylic acid (2.08 g.), ammonium chloride (0.33 g.) and sodium azide (0.36 g.) in anhydrous dimethylsulphoxide (10 ml.) was warmed on the steam bath for 16 hours. The reaction mixture was cooled, poured onto ice and kept for 16 hours. The white product was filtered off, washed with water and dried, and crystallised from aqueous ethanol to give 4-dichloromethylene-2-trichloromethybenzo[1,3]dioxin-6-carboxylic acid, m.p. 222°-223° C.

Workup

  1. temperaturewas warmed on the steam bath for 16 hours
  2. temperatureThe reaction mixture was cooled
  3. additionpoured onto ice
  4. filtrationThe white product was filtered off
  5. washwashed with water
  6. customdried
  7. customcrystallised from aqueous ethanol

Sources & evidence

ORD record
ord-20721285dce144de865526e89ff4f2a1
Source dataset
uspto-grants-1980_11
Patent number
US04232032

Reaction notes

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