Sulfamic Acid → 6,7-Bis(2,2,2-trichloroethoxycarbonyloxy)chromone-3-carboxylic acid

HRID 1105532Notes

Reaction equation

[Cl:1][C:2]([Cl:31])([Cl:30])[CH2:3][O:4][C:5]([O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[O:18][C:19]([O:21][CH2:22][C:23]([Cl:26])([Cl:25])[Cl:24])=[O:20])[O:14][CH:13]=[C:12]([CH:27]=[O:28])[C:11]2=[O:29])=[O:6].S(=O)(=O)([OH:34])N.Cl([O-])=O.[Na+]>ClCCl.O>[Cl:31][C:2]([Cl:1])([Cl:30])[CH2:3][O:4][C:5]([O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[O:18][C:19]([O:21][CH2:22][C:23]([Cl:24])([Cl:25])[Cl:26])=[O:20])[O:14][CH:13]=[C:12]([C:27]([OH:34])=[O:28])[C:11]2=[O:29])=[O:6]

Participants

Conditions

Temperature: 10 °C

Procedure

The compound (838.4 mg) obtained in Example 4, (b) was dissolved in 16 ml of dichloromethane, and with stirring at 10° C., a solution of 525 mg of sulfamic acid in 9.5 ml of water was added, followed by addition of a solution of 262.8 mg of sodium chlorite in 0.6 ml of water. The mixture was stirred for 1 hour at the same temperature. The reaction mixture was allowed to separate. The dichloromethane layer was washed with water and then with a saturated aqueous solution of sodium chloride, and then dried over magnesium sulfate. The solvent was distilled off, and the residue was recrystallized from ethyl ether to afford 685 mg of the desired product.

Workup

stirringThe mixture was stirred for 1 hour at the same temperature
customto separate
washThe dichloromethane layer was washed with water
dry with materialwith a saturated aqueous solution of sodium chloride, and then dried over magnesium sulfate
distillationThe solvent was distilled off
customthe residue was recrystallized from ethyl ether

Sources & evidence

ORD record: ord-2c8177ac15f6412393598f20ba15eb47
Source dataset: uspto-grants-1982_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04309354

Reaction notes

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