Butyl 4-aminobenzoate → Butyl 4-(p-toluenesulfonylaminocarbonylamino)benzoate

HRID 1839895Notes

Reaction equation

HRID 1839895 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:7])=[CH:4][CH:3]=1.[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>C(#N)C>[C:15]1([CH3:27])[CH:16]=[CH:17][C:18]([S:21]([NH:24][C:25]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:7])=[CH:13][CH:14]=2)=[O:26])(=[O:22])=[O:23])=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 2482Butyl 4-aminobenzoate2×HCID 77703p-Toluenesulfonyl isocyanate

Product 1

HCID 14763028Butyl 4-(p-toluenesulfonylaminocarbonylamino)benzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A three necked flask equipped with a dropping funnel, a thermometer and a reflux condenser was charged with 15.4 g of n-butyl 4-aminobenzoate and then with 150 ml of acetonitrile. The mixture in the flask was agitated to dissolve the n-butyl 4-aminobenzoate in acetonitrile. To the solution, 17.3 g of p-toluenesulfonylisocyanate were added dropwise through the dropping funnel at room temperature, while the resultant mixture was agitated by a magnetic stirrer.

Workup

  1. customA three necked flask equipped with a dropping funnel
  2. stirringwas agitated by a magnetic stirrer

Sources & evidence

ORD record
ord-ec6c6e1b1a114253829a76aad029cd4a
Source dataset
uspto-grants-2004_01
Patent number
US06677472B2

Reaction notes

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