Butyl isocyanate → 5-(n-Butylcarbamoyloxy)-1,3-benzoxathiol-2-one

HRID 1702874Notes

Reaction equation

HRID 1702874 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]([N:16]=[C:17]=[O:18])[CH2:13][CH2:14][CH3:15].C(N(CC)CC)C>C(C(C)=O)C>[CH2:12]([NH:16][C:17]([O: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)=[O:18])[CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 8110Butyl isocyanateHCID 8471TriethylamineHCID 1390671,3-Benzoxathiol-2-one, 5-hydroxy-

Product 1

HCID 130538385-(n-Butylcarbamoyloxy)-1,3-benzoxathiol-2-one

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

5-hydroxy-1,3-benzoxathiol-2-one (14.3 grams) was mixed with n-butyl isocyanate (8.85 grams) in 175 milliliters of methyl ethyl ketone in the presence of 1.3 milliliters of triethylamine. The reaction mixture was then heated at reflux temperature for 2.5 hours. The solvent was then removed from the reaction mixture by evaporation in vacuo. The off-white solid residue was recrystallized from toluene and the purified product, 5-(n-butylcarbamoyloxy)-1,3-benzoxathiol-2-one was obtained, as a white, fluffy, crystalline solid with a melting point of 99°-100° C. Elemental analysis calculated for C12H13NO4S (percent): carbon--53.92; hydrogen--4.90; nitrogen--5.24. Found: carbon--54.1; hydrogen--4.89; nitrogen--5.27.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureat reflux temperature for 2.5 hours
  3. customThe solvent was then removed from the reaction mixture by evaporation in vacuo
  4. customThe off-white solid residue was recrystallized from toluene

Sources & evidence

ORD record
ord-e052c282bc43495fbd8e68718914f49e
Source dataset
uspto-grants-1982_09
Patent number
US04349685

Reaction notes

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