HCID 21262890, compound → HCID 21262937, compound

HRID 2393638Notes

Reaction equation

HRID 2393638 reaction equation
C([NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12](/[C:15](=[C:24](/[CH2:27][CH2:28]O)\[CH2:25][OH:26])/[C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([F:23])[CH:17]=2)=[CH:11][CH:10]=1)(=[O:8])=[O:7])(C)(C)C>FC(F)(F)C(O)=O>[F:23][C:18]1[CH:17]=[C:16](/[C:15](=[C:24]2/[CH2:25][O:26][CH2:28][CH2:27]/2)/[C:12]2[CH:13]=[CH:14][C:9]([S:6]([NH2:5])(=[O:8])=[O:7])=[CH:10][CH:11]=2)[CH:21]=[CH:20][C:19]=1[CH3:22]

Participants

3

Reactant 1

HCID 21262890HCID 21262890, compound

Product 1

HCID 21262937HCID 21262937, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 6.3 g of (E) -2-[1-(4-t-butylaminosulfonylphenyl)-1-(3-fluoro-4-methylphenyl)methylidene]butane-1,4-diol prepared in Example 138 in 75 ml of trifluoroacetic acid is heated for 10 hours under reflux. The solvent is concentrated under vacuum and the residue is taken up in a dilute solution of sodium hydroxide, washed with dichloromethane and then acidified with dilute hydrochloric acid and extracted with dichloromethane. The organic phases are combined and dried over magnesium sulfate and then evaporated under vacuum. The residue is crystallized in tert-butyl methyl ether to give 4 g of (E)-4-[(3-fluoro-4-methylphenyl)-(tetrahydro-furan-3-ylidene)methyl]benzenesulfonamide in the form of crystals melting at 174°-176° C.

Workup

  1. temperatureunder reflux
  2. concentrationThe solvent is concentrated under vacuum
  3. washwashed with dichloromethane
  4. extractionextracted with dichloromethane
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under vacuum
  7. customThe residue is crystallized in tert-butyl methyl ether

Sources & evidence

ORD record
ord-194a343872f340d998fbf6da9d116165
Source dataset
uspto-grants-1998_09
Patent number
US05807873

Reaction notes

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