Thionyl Chloride → 2,4-Bis(dichloromethylidene)-2H,4H-1,3-benzodioxine-6-carbonitrile

HRID 224408Notes

Reaction equation

HRID 224408 reaction equation
[Cl:1][C:2]([Cl:19])=[C:3]1[O:8][C:7](=[C:9]([Cl:11])[Cl:10])[C:6]2[CH:12]=[C:13]([C:16]([NH2:18])=O)[CH:14]=[CH:15][C:5]=2[O:4]1.S(Cl)(Cl)=O>CN(C)C=O>[C:16]([C:13]1[CH:14]=[CH:15][C:5]2[O:4][C:3](=[C:2]([Cl:19])[Cl:1])[O:8][C:7](=[C:9]([Cl:11])[Cl:10])[C:6]=2[CH:12]=1)#[N:18]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 233329192,4-Bis(dichloromethylidene)-2H,4H-1,3-benzodioxine-6-carboxamide

Product 1

HCID 233329162,4-Bis(dichloromethylidene)-2H,4H-1,3-benzodioxine-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,4-Bis(dichloromethylene)benzo[1,3]dioxin-6-carboxamide (3.0 g.) was added in portions to a stirred mixture of thionyl chloride (15 ml.) in dimethylformamide (60 ml.) at 50° C. A precipitate rapidly formed which, after cooling the reaction mixture to ambient temperature, was filtered off, dried, and crystallised from ethanol to give 6-cyano-2,4-bis(dichloromethylene)benzo[1,3]dioxin, m.p. 167°-168° C.

Workup

  1. customA precipitate rapidly formed which
  2. filtrationwas filtered off
  3. customdried
  4. customcrystallised from ethanol

Sources & evidence

ORD record
ord-063afedfb8db45b0b151fa0eee358d80
Source dataset
uspto-grants-1980_11
Patent number
US04232032

Reaction notes

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