Triethylamine → 5-[3-(Trifluoromethyl)phenylcarbamoyloxy]-1,3-benzoxathiol-2-one

HRID 1702871Notes

Reaction equation

HRID 1702871 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](=[O:10])[S:7][C:6]=2[CH:11]=1.[F:12][C:13]([F:24])([F:23])[C:14]1[CH:15]=[C:16]([N:20]=[C:21]=[O:22])[CH:17]=[CH:18][CH:19]=1.C(N(CC)CC)C>C(C(C)=O)C>[F:12][C:13]([F:23])([F:24])[C:14]1[CH:15]=[C:16]([NH:20][C:21]([O:1][C:2]2[CH:3]=[CH:4][C:5]3[O:9][C:8](=[O:10])[S:7][C:6]=3[CH:11]=2)=[O:22])[CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 1390671,3-Benzoxathiol-2-one, 5-hydroxy-

Product 1

HCID 130538345-[3-(Trifluoromethyl)phenylcarbamoyloxy]-1,3-benzoxathiol-2-one

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

5-hydroxy-1,3-benzoxathiol-2-one (16.8 grams) was mixed with 3-(trifluoromethyl)phenyl isocyanate (18.7 grams) and 1.01 grams of triethylamine in 200 milliliters of methyl ethyl ketone. This solution was heated at reflux temperature for one hour, after which the solvent was removed by evaporation in vacuo. The resulting residue was recrystallized twice from ethyl acetate, leaving the desired purified product, 5-[3-(trifluoromethyl)phenylcarbamoyloxy]-1,3-benzoxathiol-2-one. The product was a white crystalline solid which exhibited a melting point of 166.5°-168° C. Elemental analysis calculated for C15H8F3NO4S (percent): carbon--50.71; hydrogen--2.27; nitrogen--3.94. Found: carbon--51.0; hydrogen--2.29; nitrogen--4.11.

Workup

  1. temperatureThis solution was heated
  2. temperatureat reflux temperature for one hour
  3. customafter which the solvent was removed by evaporation in vacuo
  4. customThe resulting residue was recrystallized twice from ethyl acetate
  5. customleaving the
  6. customdesired purified product, 5-[3-(trifluoromethyl)phenylcarbamoyloxy]-1,3-benzoxathiol-2-one

Sources & evidence

ORD record
ord-bd9a24e6d14441a49224829566165592
Source dataset
uspto-grants-1982_09
Patent number
US04349685

Reaction notes

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