Methyl 4-aminobenzoate → Methyl 4-methanesulfonamidobenzoate

HRID 1992235

Reaction equation

HRID 1992235 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[S:12](Cl)([CH3:15])(=[O:14])=[O:13].C(N(CC)C(C)C)C>C(Cl)Cl>[CH3:15][S:12]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1)(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 12082Methyl 4-aminobenzoateHCID 31297Methanesulfonyl chlorideHCID 521913N,N-Diethyl-2-propanamine

Product 1

HCID 669159Methyl 4-methanesulfonamidobenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.13 g (7.48 mmol) of methyl 4-aminobenzoate was dissolved in 20 mL of anhydrous DCM and 1.97 g (17.19 mmol) of mesyl chloride was added at 4 deg C., followed by the 2.22 g (17.19 mmol) of the diethylisopropylamine. Reaction was carried out overnight at room temperature resulting methyl 4-[(methylsulfonyl)amino]benzoate, which was used in the next step without additional purification.

Workup

  1. customReaction

Sources & evidence

ORD record
ord-7f5f7b731cca4810b466e6e67807f8d0
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Linked notes

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