1,4-Dioxane → P-Phenylenediamine

HRID 1580910Notes

Reaction equation

HRID 1580910 reaction equation
ClS(C1C=C(C(O)=O)C(=CC=1)C(O)=O)(=O)=O.[OH:17][C:18]1[C:31]2[C:30](=[O:32])[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23](=[O:33])[C:22]=2C([NH:34][C:35]2[CH:40]=[CH:39][C:38]([NH2:41])=[CH:37][CH:36]=2)=C[CH:19]=1.[O:42]1[CH2:47][CH2:46]OCC1>>[CH2:46]1[C:47](=[O:42])[C:22]2[C:31](=[C:30]([OH:32])[C:29]3[C:24]([C:23]=2[OH:33])=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:18](=[O:17])[CH2:19]1.[CH:36]1[C:35]([NH2:34])=[CH:40][CH:39]=[C:38]([NH2:41])[CH:37]=1

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 12956245HCID 12956245, compoundHCID 20194322HCID 20194322, compound

Product 2

HCID 7814P-PhenylenediamineHCID 872111,4-Anthracenedione, 2,3-dihydro-9,10-dihydroxy-

Procedure

1 part of 4-chlorosulphonyl phthalic acid is added to a solution of 0.5 parts of 1-hydroxy-4-(4-aminoanilino)-anthraquinone, (itself obtained by the reaction of leucoquinizarin with 4-phenylene diamine) in 25 parts of dioxan. The mixture is heated under reflux for 51/2 hours, filtered hot, and the filtrate poured into water. The precipitated product is filtered off, dissolved in dilute sodium carbonate solution at 20°C, screened, and the filtrate acidified with mineral acid to give 0.4 parts of 1-hydroxy-4-[4-(3,4-dicarboxy phenylsulphonylamino)anilino]anthraquinone.

Sources & evidence

ORD record
ord-522bf73489354a3a812cccf8c9222168
Source dataset
uspto-grants-1976_01
Patent number
US03934972

Reaction notes

Loading…