Triethylamine → 5-[(3-Ethylphenyl)carbamoyloxy]-1,3-benzoxathiol-2-one

HRID 1702873Notes

Reaction equation

HRID 1702873 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.[CH2:12]([C:14]1[CH:15]=[C:16]([N:20]=[C:21]=[O:22])[CH:17]=[CH:18][CH:19]=1)[CH3:13].C(N(CC)CC)C>C(C(C)=O)C>[CH2:12]([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)[CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1390671,3-Benzoxathiol-2-one, 5-hydroxy-HCID 27696373-Ethylphenyl isocyanate

Product 1

HCID 130538375-[(3-Ethylphenyl)carbamoyloxy]-1,3-benzoxathiol-2-one

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

5-hydroxy-1,3-benzoxathiol-2-one (15.0 grams) was mixed with 3-ethylphenyl isocyanate (13.1 grams) in 180 milliliters of methyl ethyl ketone in the presence of 0.90 gram of triethylamine. This solution was heated at reflux temperature with stirring for 3 hours and 15 minutes. The solvent was then removed by evaporation in vacuo and the residual, viscous oil was dissolved in a hot mixture of ethyl acetate and methylcyclohexane. Upon slowly cooling to room temperature, the solution gave the purified 5-[(3-ethylphenyl)carbamoyloxy]-1,3-benzoxathiol-2-one as a white crystalline solid with a melting point of 96°-97° C. Elemental analysis calculated for C16H13NO4S (percent): carbon--60.94; hydrogen--4.15; nitrogen--4.44. Found: carbon--61.2; hydrogen--4.26; nitrogen--4.54.

Workup

  1. temperatureThis solution was heated
  2. temperatureat reflux temperature
  3. customThe solvent was then removed by evaporation in vacuo
  4. dissolutionthe residual, viscous oil was dissolved in a hot mixture of ethyl acetate and methylcyclohexane

Sources & evidence

ORD record
ord-087603cbd95a46daa54de89dfe09788f
Source dataset
uspto-grants-1982_09
Patent number
US04349685

Reaction notes

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