2,3,5,6-Tetrachloroaniline → HCID 21836024, compound
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]=1[F:20].[Cl:21][C:22]1[C:28]([Cl:29])=[CH:27][C:26]([Cl:30])=[C:25]([Cl:31])[C:23]=1[NH2:24]>>[Cl:21][C:22]1[C:28]([Cl:29])=[CH:27][C:26]([Cl:30])=[C:25]([Cl:31])[C:23]=1[NH:24][C:4]1[C:3]([F:20])=[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].[Cl:21][C:22]1[C:28]([Cl:29])=[CH:27][C:26]([Cl:30])=[C:25]([Cl:31])[C:23]=1[NH:24][C:4]1[C:3]([NH:24][C:23]2[C:25]([Cl:31])=[C:26]([Cl:30])[CH:27]=[C:28]([Cl:29])[C:22]=2[Cl:21])=[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]Participants
Procedure
2 g of 1,2,3,4-Tetrafluoroanthraquinone and 30 g of 2,3,5,6-tetrachloroaniline were charged in a 50 cc, four necked flask and then the reaction was carried out at 210° C. for about 10 hours. After completion of reaction, 2,3,5,6-tetrachloroaniline was distilled out from the reaction solution and a column purification thereof using a column with a silica gel was effected to give rise to 0.62 g of 2-(2,3,5,6-tetrachloroanilino)-1,3,4-trifluoroanthraquinone (Dye 11') (yield 17.8 mol %) and 0.53 g of 2,3-bis(2,3,5,6-tetrachloroanilino)-1,4-difluoroanthraquinone (Dye 27') (yield 10.6 mol %). The physical properties of Dye 11' and analytical values defining the compound are tabulated in Table 22 and the physical properties of Dye 27' and analytical values defining the compound are tabulated in Table 23.
Workup
- distillationwas distilled out from the reaction solution
- customa column purification
Sources & evidence
- ORD record
- ord-bafffc5473504cdd8e9d58c8e0fd27d3
- Source dataset
- uspto-grants-1999_10
- Patent number
- US05968688
Reaction notes
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