Water → HCID 368387, compound

HRID 1590702Notes

Reaction equation

HRID 1590702 reaction equation
[CH2:1]([N:3]([CH2:31][CH3:32])[CH2:4][CH:5]([OH:30])[CH2:6][NH:7][C:8]1[C:21]2[C:20](=[O:22])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=[O:23])[C:12]=2[C:11]([NH:24][CH2:25][CH:26]([OH:29])[CH2:27][Cl:28])=[CH:10][CH:9]=1)[CH3:2].O>CC(C)=O.ClCCl>[ClH:28].[CH2:31]([N:3]([CH2:1][CH3:2])[CH2:4][CH:5]([OH:30])[CH2:6][NH:7][C:8]1[C:21]2[C:20](=[O:22])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=[O:23])[C:12]=2[C:11]([NH:24][CH2:25][CH:26]([OH:29])[CH2:27][Cl:28])=[CH:10][CH:9]=1)[CH3:32]

Participants

4

Reactant 2

HCID 962WaterHCID 368388HCID 368388, compound

Product 1

HCID 368387HCID 368387, compound

Reagents, catalysts & solvents 1

HCID 21584124Propan-2-one--dichloromethane (1/1)Solvent

Procedure

Concentrated HC1 (8 drops) was slowly added to a solution of 1-(3-diethylamino-2-hydroxypropylamino)-4-(3-chloro-2-hydroxypropylamino)-9, 10-anthracenedione (0.531 g, 2.36 mmol) in acetone-dichloromethane (50%, 15 mL). A color change from purple to red was observed. The solid was obtained by filtration, mp 106°-108° C., extremely hygroscopic. 1H NMR (D2O) δ 1.40 (t, J=7.3 Hz, 6H, CH3), 2.90 (m, 4H, CH2), 3.29 (m, 4H, CH2), 3.38 (m, 3H, CH2, CH), 3.73 (m, 3H, CH2, CH), 3.92 (broad, 1H, NH), 4.15 (broad, 1H, NH), 6.23 (s, 2H, ArH (2, 3)), 7.26 (m, 2H, ArH (6, 7)), 7.32 (m, 2H, ArH (5, 8)). Anal. Calcd for C24H30ClN 3 O4 2HCl 1.5 H2O: C, 51.48; H, 6.30; N, 7.50. Found: C, 51.70; H, 6.35; N, 7.41.

Workup

  1. concentrationConcentrated HC1 (8 drops)
  2. customThe solid was obtained by filtration, mp 106°-108° C.

Sources & evidence

ORD record
ord-ad1722f6f2404750aa4e6b121947964f
Source dataset
uspto-grants-1993_04
Patent number
US05204370

Reaction notes

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