Pyridine → 4-(Methylsulfonamido)benzoic acid

HRID 463671

Reaction equation

HRID 463671 reaction equation
N1C=CC=CC=1.[NH2:7][C:8]1[CH:18]=[CH:17][C:11]([C:12]([O:14]CC)=[O:13])=[CH:10][CH:9]=1.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>ClCCl>[CH3:19][S:20]([NH:7][C:8]1[CH:18]=[CH:17][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=1)(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 1049PyridineHCID 2337BenzocaineHCID 31297Methanesulfonyl chloride

Product 1

HCID 2506534-(Methylsulfonamido)benzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To 215.2 g (2.72 mole) of pyridine in 1250 ml of dichloromethane is added 238 g (1.44 mole) of ethyl 4-aminobenzoate. After cooling to 0° C., a solution of 177.6 g (1.55 mole) of methanesulfonyl chloride in 250 ml of dichloromethane is added with stirring. Upon completion of the addition, the ice bath is removed and the reaction is stirred for one hour at room temperature.

Workup

  1. additionUpon completion of the addition
  2. customthe ice bath is removed
  3. stirringthe reaction is stirred for one hour at room temperature

Sources & evidence

ORD record
ord-98f76ec3828f43fabcd0c535838e6578
Source dataset
uspto-grants-1985_10
Patent number
US04544654

Linked notes

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