Isopropylamine → HCID 13763878, compound

HRID 1252976Notes

Reaction equation

HRID 1252976 reaction equation
S(O[C:12]1[C:25]2[C:24](=[O:26])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17](=[O:27])[C:16]=2[C:15]([O:28][S:29]([C:32]2[CH:38]=[CH:37][C:35]([CH3:36])=[CH:34][CH:33]=2)(=[O:31])=[O:30])=[CH:14][CH:13]=1)(C1C=CC(C)=CC=1)(=O)=O.[CH:39]([NH2:42])([CH3:41])[CH3:40]>>[CH:39]([NH:42][C:12]1[C:25]2[C:24](=[O:26])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17](=[O:27])[C:16]=2[C:15]([O:28][S:29]([C:32]2[CH:38]=[CH:37][C:35]([CH3:36])=[CH:34][CH:33]=2)(=[O:31])=[O:30])=[CH:14][CH:13]=1)([CH3:41])[CH3:40]

Participants

3

Reactant 2

HCID 6363IsopropylamineHCID 3841169,10-Anthracenedione, 1,4-bis[[(4-methylphenyl)sulfonyl]oxy]-

Product 1

HCID 13763878HCID 13763878, compoundYield 76%

Procedure

1-(isopropylamino)-4-tosyloxyanthraquinone was prepared by reaction of 1,4-ditosyloxyanthraquinone with isopropyl amine. The isolated and purified reaction product has the structure illustrated below (where "Ts" is ##STR8## The yield was 76% and the m.p. 164°-165° C.; mass spec m/e/ 435 (M+), 420 (M-CH3), 280 (M-C7H7SO2), 238 (280-CH3H7 +H), 210 (238-CO), 182 (210-CO), 155 (C7H7SO2), 91 (C7H7); 1H-NMR (CD2Cl2)δ9.97 (br s, 1H), 8.19-8.10 (m, 2H), 7.85-7.67 (m, 4H), 7.27-6.97 (m, 4H), 4.02-3.68 (m, 1H), 2.30 (s, 3H), 1.38, 1.31 (d, 6H); IR (Nujol) 1180 cm-1 (symmetrical SO2 stretch), 890 cm-1, 860, 820, 780 (S--O--C stretch); UV/VIS max (Xylenes(500 nm (ε6660).

Workup

  1. customThe isolated
  2. custompurified
  3. customreaction product

Sources & evidence

ORD record
ord-7822c0891bbd47f6a7a8fb76522996a9
Source dataset
uspto-grants-1988_05
Patent number
US04746461

Reaction notes

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