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

HRID 1105532
Notes
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Reaction equation

HRID 1105532 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 5987Sulfamic AcidHCID 12800626HCID 12800626, compound2×HCID 23668197Sodium Chlorite

Product 1

HCID 128006276,7-Bis(2,2,2-trichloroethoxycarbonyloxy)chromone-3-carboxylic acidYield 79.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×
HCID 6344
Dichloromethane
Solvent

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

  1. stirringThe mixture was stirred for 1 hour at the same temperature
  2. customto separate
  3. washThe dichloromethane layer was washed with water
  4. dry with materialwith a saturated aqueous solution of sodium chloride, and then dried over magnesium sulfate
  5. distillationThe solvent was distilled off
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes