Aniline → N~2~,N~4~,N~6~-Tris(4-aminophenyl)-1,3,5-triazine-2,4,6-triamine

HRID 1604047Notes

Reaction equation

HRID 1604047 reaction equation
C1(N=[N:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[N:21]=[C:20]([NH:22][C:23]4[CH:28]=[CH:27][C:26]([N:29]=NC5C=CC=CC=5)=[CH:25][CH:24]=4)[N:19]=[C:18]([NH:37][C:38]4[CH:43]=[CH:42][C:41]([N:44]=NC5C=CC=CC=5)=[CH:40][CH:39]=4)[N:17]=3)=[CH:11][CH:10]=2)C=CC=CC=1.O.NN.NC1C=CC=CC=1>[Pd].C(O)C(C)C>[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[N:21]=[C:20]([NH:22][C:23]3[CH:24]=[CH:25][C:26]([NH2:29])=[CH:27][CH:28]=3)[N:19]=[C:18]([NH:37][C:38]3[CH:43]=[CH:42][C:41]([NH2:44])=[CH:40][CH:39]=3)[N:17]=2)=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 6115AnilineHCID 24654Hydrazine hydrate (1:1)HCID 10876106HCID 10876106, compound

Product 1

HCID 11003879N~2~,N~4~,N~6~-Tris(4-aminophenyl)-1,3,5-triazine-2,4,6-triamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6560IsobutanolSolvent

Conditions

Temperature
70 °C

Procedure

In one 100 milliliter, four-neck, round-bottom flask equipped with a thermo-couple, a condenser, a mechanical stirrer, and a nitrogen sweep were placed 3.34 grams (0.005 mole) of 2,4,6-tris-[4-(phenylazo)phenylamino]-1,3,5-triazine, 50 grams of isobutanol, 1.66 grams (0.033 mole) of hydrazine hydrate and 0.15 gram of 5 percent palladium on carbon (approximately 60 percent wet). Over a period of two hours, the mixture was heated to 70° C., and held an additional ten hours at 70° C. The reduction was followed by high performance liquid chromatography by observing the disappearance of the starting tris-azo compound and the conversion of the intermediate di- and mono-azo compounds to the tris-amino compound and the formation of the by-product aniline. The title compound was isolated by filtration at 60° C. The filter cake was washed with 10 milliliters of isobutanol, dried to a constant weight to give 100 percent yield (2 grams) of 2,4,6-tris-[4-aminoanilino]-1,3,5-triazine. The melt point was 297°-299° C. The infrared spectrum was consistent with the structure. Relative area HPLC analysis showed it to be 97.8 percent pure. The filtrate was distilled to recover 1.1 grams of aniline, 78.6 percent of theory.

Workup

  1. waitheld an additional ten hours at 70° C

Sources & evidence

ORD record
ord-72ffa0716b5045d98445c87d06049f48
Source dataset
uspto-grants-1999_11
Patent number
US05990310

Reaction notes

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