Water → HCID 10067138, compound

HRID 374649Notes

Reaction equation

HRID 374649 reaction equation
[NH2:1][C:2]1[CH:15]=[C:14]([O:16][CH3:17])[C:13]2[C:12](=[O:18])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][C:10]=3[O:19][CH3:20])[C:5](=[O:21])[C:4]=2[CH:3]=1.[CH3:22][S:23](Cl)(=[O:25])=[O:24].O>N1C=CC=CC=1>[CH3:17][O:16][C:14]1[C:13]2[C:12](=[O:18])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][C:10]=3[O:19][CH3:20])[C:5](=[O:21])[C:4]=2[CH:3]=[C:2]([NH:1][S:23]([CH3:22])(=[O:25])=[O:24])[CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 18996959HCID 18996959, compound

Product 1

HCID 10067138HCID 10067138, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
90 °C

Procedure

2-Amino-9,10-dihydro-4,5-dimethoxy-9,10-dioxoanthracene (1.5 g) was dissolved in dry pyridine (30 ml) and freshly distilled methanesulphonyl chloride (0.61 g) slowly added. The mixture was heated to 90° C. for 3 hours under an atmosphere of nitrogen before being allowed to cool to room temperature. The mixture was then poured into water (150 ml), generating a brown precipitate. The solid was collected by filtration and dried in vacuo over silica gel to yield N-(4,5-dimethoxy-9,10-dihydro-9,10-dioxoanthracen-2-yl)methanesulphonamide at 94% purity (HPLC) as brown lustrous crystals. To improve purity, the crystals were dissolved in 2N sodium hydroxide solution, washed with CHCl3, and filtered to remove any remaining solid residue.

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe solid was collected by filtration
  3. customdried in vacuo over silica gel

Sources & evidence

ORD record
ord-f391a51001e548348a208676f1b2b23c
Source dataset
uspto-grants-1996_01
Patent number
US05480873

Reaction notes

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