Dibenzyl ether → HCID 13261521, compound

HRID 2295465Notes

Reaction equation

HRID 2295465 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:10]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22]CC2C=CC=CC=2)(=[O:15])=[O:14])=[O:11])[N:3]=1.C(OCC1C=CC=CC=1)C1C=CC=CC=1>FC(F)(F)C(O)=O.CC(C)=O>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:10]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[OH:22])(=[O:15])=[O:14])=[O:11])[N:3]=1

Participants

5

Reactant 2

HCID 7657Dibenzyl etherHCID 13261520HCID 13261520, compound

Product 1

HCID 13261521HCID 13261521, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A stirred solution of 0.5 g of N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-(benzyloxy)benzenesulfonamide (from b, above) in 20 ml of trifluoroacetic acid was boiled under reflux for 1.5 hours. The proton magnetic resonance spectrum indicated complete cleavage of the benzyl ether. The trifluoroacetic acid was evaporated in vacuum and the oily residue stirred with water and diethyl ether, providing white solid. The solid was dissolved in acetone and reprecipitated by dilution of the solution with hexane, yielding N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-hydroxybenzenesulfonamide as a white solid, m.p. ca. 180°. The mass spectrum showed a molecular ion, m/e 322; ##STR38## and no m/e 91 (no Ph--CH2+).

Workup

  1. temperatureunder reflux for 1.5 hours
  2. customThe trifluoroacetic acid was evaporated in vacuum
  3. customproviding white solid
  4. customreprecipitated by dilution of the solution with hexane

Sources & evidence

ORD record
ord-7bc554b17fa84913a9049a61f0258aaa
Source dataset
uspto-grants-1984_01
Patent number
US04425153

Reaction notes

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