2,4-Bis(trichloromethyl)-2H,4H-1,3-benzodioxine-6-carboxamide → 2,4-Bis(dichloromethylidene)-2H,4H-1,3-benzodioxine-6-carboxamide

HRID 224407Notes

Reaction equation

HRID 224407 reaction equation
[Cl:1][C:2](Cl)([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]([NH2:19])=[O:18])[CH:15]=[CH:16][C:5]=2[O:4]1.CC(C)([O-])C.[K+]>CS(C)=O>[Cl:20][C:2]([Cl:1])=[C:3]1[O:8][C:7](=[C:9]([Cl:11])[Cl:10])[C:6]2[CH:13]=[C:14]([C:17]([NH2:19])=[O:18])[CH:15]=[CH:16][C:5]=2[O:4]1

Participants

4

Reactant 2

HCID 233329312,4-Bis(trichloromethyl)-2H,4H-1,3-benzodioxine-6-carboxamideHCID 23665647Potassium tert-butoxide

Product 1

HCID 233329192,4-Bis(dichloromethylidene)-2H,4H-1,3-benzodioxine-6-carboxamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 2,4-bis(trichloromethyl)benzo[1,3]dioxin-6-carboxamide (3.14 g.) and potassium t-butoxide (2.5 g.) in 50% aqueous dimethylsulphoxide (50 ml.) was heated at 80°-90° C. for 2 hours. The solid product was filtered off, dried and crystallised from ethanol to give 2,4-bis(dichloromethylene)benzo[1,3]dioxin-6-carboxamide, m.p. 217°-218° C.

Workup

  1. temperaturewas heated at 80°-90° C. for 2 hours
  2. filtrationThe solid product was filtered off
  3. customdried
  4. customcrystallised from ethanol

Sources & evidence

ORD record
ord-d1c62ccbd39e4b7fbf062e1a479fff8a
Source dataset
uspto-grants-1980_11
Patent number
US04232032

Reaction notes

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