Aniline → 4,4'-bis(2-morpholino-4-anilino-s-triazinyl-6-amino)stilbene-2,2'-disulfonic acid disodium salt

HRID 1606231

Reaction equation

HRID 1606231 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([S:21]([O-:24])(=[O:23])=[O:22])[C:5]([CH:8]=[CH:9][C:10]2[C:11]([S:17]([O-:20])(=[O:19])=[O:18])=[CH:12][C:13]([NH2:16])=[CH:14][CH:15]=2)=[CH:6][CH:7]=1.[Na+:25].[Na+].N1C(Cl)=NC(Cl)=NC=1Cl.ClC1N=C(Cl)N=C(NC2C=C(S([O-])(=O)=O)C(C=C[C:53]3[C:54](S([O-])(=O)=O)=[CH:55][C:56]([NH:59][C:60]4[N:65]=[C:64](Cl)[N:63]=[C:62](Cl)[N:61]=4)=[CH:57][CH:58]=3)=CC=2)N=1.[Na+].[Na+].NC1C=CC=CC=1.[NH:85]1[CH2:90][CH2:89][O:88][CH2:87][CH2:86]1.ClC1N=C(NC2C=CC=CC=2)N=C(NC2C=C(S([O-])(=O)=O)C(C=CC3C(S([O-])(=O)=O)=CC(NC4N=C(Cl)N=C(NC5C=CC=CC=5)N=4)=CC=3)=CC=2)N=1.[Na+].[Na+].Cl[C:146]1[N:151]=[C:150]([N:152]2[CH2:157][CH2:156][O:155][CH2:154][CH2:153]2)[N:149]=[C:148]([NH:158][C:159]2[CH:160]=[C:161](S([O-])(=O)=O)[C:162](C=CC3C(S([O-])(=O)=O)=CC(NC4N=C(Cl)N=C(N5CCOCC5)N=4)=CC=3)=[CH:163][CH:164]=2)[N:147]=1.[Na+].[Na+]>>[NH:158]([C:148]1[N:149]=[C:150]([N:152]2[CH2:157][CH2:156][O:155][CH2:154][CH2:153]2)[N:151]=[C:146]([NH:1][C:2]2[CH:3]=[C:4]([S:21]([O-:24])(=[O:23])=[O:22])[C:5]([CH:8]=[CH:9][C:10]3[C:11]([S:17]([O-:20])(=[O:19])=[O:18])=[CH:12][C:13]([NH:16][C:62]4[N:61]=[C:60]([NH:59][C:56]5[CH:57]=[CH:58][CH:53]=[CH:54][CH:55]=5)[N:65]=[C:64]([N:85]5[CH2:90][CH2:89][O:88][CH2:87][CH2:86]5)[N:63]=4)=[CH:14][CH:15]=3)=[CH:6][CH:7]=2)[N:147]=1)[C:159]1[CH:164]=[CH:163][CH:162]=[CH:161][CH:160]=1.[Na+:25].[Na+:25]

Participants

8

Reactant 7

HCID 6115Aniline2×HCID 7954Cyanuric chlorideHCID 8083Morpholine2×HCID 169857Benzenesulfonic acid, 2,2'-(1,2-ethenediyl)bis[5-[[4-chloro-6-(phenylamino)-1,3,5-triazin-2-yl]amino]-, disodium saltHCID 28374734,4'-diamino-2,2'-stilbenedisulfonic acid, disodium saltHCID 57376756Disodium 4,4'-bis-(4-chloro-6-morpholino-s-triazin-2-ylamino)-2,2'-stilbene disulfonateHCID 73156169Disodium 4,4'-bis(4,6-dichloro-s-triazin-2-ylamino)-2,2'-stilbenedisulfonate

Product 1

HCID 276774,4'-bis(2-morpholino-4-anilino-s-triazinyl-6-amino)stilbene-2,2'-disulfonic acid disodium salt

Procedure

are known compounds which have valuable properties as fluorescent optical bleaching agents in detergent compositions for the laundering of textile goods. The preparation of these compounds is ordinarily carried out as follows. One molecular proportion of disodium 4,4'-diaminostilbene-2,2'-disulfonate is condensed with two molecular proportions of cyanuric chloride at low temperature (0°-5° C.); then, in the case of the compound of Formula I, one molecular proportion of the resulting disodium 4,4'-bis(4,6-dichloro-s-triazin-2-ylamino)-2,2'-stilbenedisulfonate is aminated with two molecular proportions of aniline or morpholine at approximately 50° C.; and one molecular proportion of the resulting product, that is, disodium 4,4'-bis(4-chloro-6-anilino-s-triazin-2-ylamino)-2,2'-stilbenedisulfonate or disodium 4,4'-bis-(4-chloro-6-morpholino-s-triazin-2-ylamino)-2,2'-stilbene disulfonate is aminated at 95°-100° C. with two molecular proportions of either morpholine or aniline, respectively, to produce disodium 4,4'-bis(4-anilino-6-morpholino-s-triazin-2-ylamino)-2,2'-stilbenedisulfonate. In the case of the compound of Formula II, the intermediate disodium 4,4'-bis(4,6-dichloro-s-triazin-2-ylamino)-2,2'-disulfonate is interacted with aniline at a somewhat higher temperature (usually in the range 30°-100° C.) to replace the four chloro substituents with four anilino groups. In each of these steps, sufficient alkali is added to the reaction mixture to keep it substantially neutral during the reaction.

Workup

  1. customThe preparation of these compounds

Sources & evidence

ORD record
ord-52ff6034387348a885f9a5e64cf7d1a0
Source dataset
uspto-grants-1976_04
Patent number
US03951960

Linked notes

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