p-Toluenesulfonyl isocyanate → Butyl 3-(p-toluenesul-fonylamino carbonylamino)benzoate

HRID 24979

Reaction equation

HRID 24979 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[C:5]([O:7][CH2:8][CH2:9][CH2:10][CH3:11])=[O:6].[C:15]1([CH3:27])[CH:20]=[CH:19][C:18]([S:21]([N:24]=[C:25]=[O:26])(=[O:23])=[O:22])=[CH:17][CH:16]=1>C1(C)C=CC=CC=1>[C:15]1([CH3:27])[CH:16]=[CH:17][C:18]([S:21]([NH:24][C:25]([NH:1][C:2]2[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=2)[C:5]([O:7][CH2:8][CH2:9][CH2:10][CH3:11])=[O:6])=[O:26])(=[O:22])=[O:23])=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 77703p-Toluenesulfonyl isocyanateHCID 15914845Butyl 3-aminobenzoate2×

Product 1

HCID 22564747Butyl 3-(p-toluenesul-fonylamino carbonylamino)benzoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a three-necked flask equipped with a dropping funnel, a thermometer and a reflux condenser 15.4 g of n-butyl 3-aminobenzoate was placed and 150 ml of toluene was added thereto with stirring to dissolve n-butyl 3-aminobenzoate therein. With stirring the resultant mixture by a magnetic stirrer, 17.3 g of p-toluenesulfonylisocyanate was added dropwise to the mixture through the dropping funnel at room temperature. Continuous stirring of the reaction mixture caused an exothermic reaction, thereby precipitating a large amount of white solid.

Workup

  1. customIn a three-necked flask equipped with a dropping funnel
  2. stirringContinuous stirring of the reaction mixture
  3. customan exothermic reaction
  4. customprecipitating a large amount of white solid

Sources & evidence

ORD record
ord-a8b49f6aefc542ba8571859e841a038a
Source dataset
uspto-grants-2005_02
Patent number
US06858565B2

Linked notes

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