Aniline → HCID 20205653, compound

HRID 543060Notes

Reaction equation

HRID 543060 reaction equation
[S:1]([C:11]1[C:24]2[C:23](=[O:25])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16](=[O:26])[C:15]=2[C:14](S(C2C=CC(C)=CC=2)(=O)=O)=[CH:13][CH:12]=1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[NH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>>[NH:37]([C:14]1[C:15]2[C:16](=[O:26])[C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:23](=[O:25])[C:24]=2[C:11]([S:1]([C:4]2[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=2)(=[O:3])=[O:2])=[CH:12][CH:13]=1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

3

Reactant 2

HCID 6115AnilineHCID 20205654HCID 20205654, compound

Product 1

HCID 20205653HCID 20205653, compoundYield 79%

Procedure

1-(anilino)-4-tosylanthraquinone was prepared by reaction of 1,4-ditosylanthraquinone with aniline. The isolated and purified reaction product has the structure illustrated below (where "Ts" is ##STR12## The yield was 79% and the m.p. 185°-186° C. Mass spec m/e 469 (M+), 314 (M-C7H7SO2), 155 (C7H7SO2), 91 (C7H7); H-NMR (CD2Cl2)δ11.50 (br s, 1H), 8.26-8.12 (m, 2H), 8.02-7.84 (m, 2H), 7.79-7.62 (m, 4H), 7.54-7.13 (m, 7H), 2.31 (s, 3H); IR (Nujol) 1355 cm-1 (asymmetric SO2 stretch), 1184 cm-1 (symmetrical SO2 stretch), 945 cm-1, 872, 840, 822, 810, 800, 788, 755 (S--O--C stretch); UV/VIS max (Xylenes) 500 nm (ε7000).

Workup

  1. customThe isolated
  2. custompurified
  3. customreaction product

Sources & evidence

ORD record
ord-eb32730926f248d48e6f40e641f85061
Source dataset
uspto-grants-1987_04
Patent number
US04661293

Reaction notes

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