HCID 19826030, compound → HCID 19826014, compound

HRID 1086453Notes

Reaction equation

HRID 1086453 reaction equation
[C:1]1([S:19]([Cl:22])(=[O:21])=[O:20])[C:14]2[C:5](=[N:6][C:7]3[C:12]([CH:13]=2)=[C:11](S(Cl)(=O)=O)[CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1>C(OCC)(=O)C>[C:1]1([S:19]([Cl:22])(=[O:20])=[O:21])[C:14]2[C:5](=[N:6][C:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 19826030HCID 19826030, compound

Product 1

HCID 19826014HCID 19826014, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Add acridine (5 g, 28 mmol) in portions to chlorosulfonic acid (7 mL, 2.2 eq) over 5 minutes with efficient stirring. Heat the reaction mixture to reflux for 5 hours. Cool the reaction mixture to room temperature and add cautiously to crushed ice (200 mL). Adjust the suspension to alkaline pH (phenolphthalein indicator) with sodium bicarbonate solid added in portions. Extract with methylene chloride (100 mL), wash the organic layer with saturated aqueous sodium carbonate (100 mL), saturated aqueous sodium chloride (100 mL). Dry the organic layer (MgSO4), filter and concentrate in vacuo to give an orange solid. Chromatograph on a column of silica gel (800 mL) eluting with 3:2 ethyl acetate:hexane to give the sulfonyl chloride as an apparent mixture of isomers (2.71 g) and the acridine-1,8-disulfonyl chloride (2.28 g) side product, both as yellow solids. Rf=0.85 (mono), 0.50 (di) (100% ethyl acetate)

Workup

  1. additionas an apparent mixture of isomers (2.71 g)

Sources & evidence

ORD record
ord-678193ffaa1e48768aaa54176b68961d
Source dataset
uspto-grants-1991_07
Patent number
US05030631

Reaction notes

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