1,2-Benzenedicarbonitrile, 4-amino- → HCID 21836013, compound

HRID 1739626Notes

Reaction equation

HRID 1739626 reaction equation
[F:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5]([F:18])=[C:4](F)[C:3]=1F.[C:21]([C:23]1[CH:24]=[C:25]([CH:27]=[CH:28][C:29]=1[C:30]#[N:31])[NH2:26])#[N:22]>ClC1C2C(=CC=CC=2)C=CC=1>[C:21]([C:23]1[CH:24]=[C:25]([CH:27]=[CH:28][C:29]=1[C:30]#[N:31])[NH:26][C:4]1[C:3]([NH:26][C:25]2[CH:27]=[CH:28][C:29]([C:30]#[N:31])=[C:23]([C:21]#[N:22])[CH:24]=2)=[C:2]([F:1])[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5]=1[F:18])#[N:22]

Participants

4

Reactant 2

HCID 925291,2-Benzenedicarbonitrile, 4-amino-2×HCID 2833793HCID 2833793, compound

Product 1

HCID 21836013HCID 21836013, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 70031-ChloronaphthaleneSolvent2×

Procedure

2 g of 1,2,3,4-Tetrafluoroanthraquinone, 35 g of 3,4-dicyanoaniline and 60 ml of α-chloronaphthalene were charged in a 200 cc, four necked flask and then the reaction was carried out at 180° C. for about 9 hours. After completion of reaction, 3,4-dicyanoaniline and α-chloronaphthalene were distilled out from the reaction solution and then a column purification using a column with a silica gel was effected to give rise to 2.95 g of 2,3-bis(3,4-dicyanoanilino)-1,4-difluoroanthraquinone (Dye 26') (yield 78.5 mol %). The physical properties of Dye 26' and analytical values defining the compound are tabulated in Table 23. Its UV spectral is shown in FIG. 6.

Workup

  1. distillationwere distilled out from the reaction solution
  2. customa column purification

Sources & evidence

ORD record
ord-7da80e4eeec44bcea71e2abafc06079a
Source dataset
uspto-grants-1999_10
Patent number
US05968688

Reaction notes

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