4-Toluenesulfonyl chloride → 2-(Toluene-4-sulfonylamino)-benzoic acid methyl ester

HRID 2389546Notes

Reaction equation

HRID 2389546 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[S:12](Cl)([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13]>N1C=CC=CC=1>[CH3:19][C:18]1[CH:20]=[CH:21][C:15]([S:12]([NH:1][C:2]2[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=2[C:4]([O:6][CH3:7])=[O:5])(=[O:14])=[O:13])=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 8635Methyl Anthranilate

Product 1

HCID 7376052-(Toluene-4-sulfonylamino)-benzoic acid methyl esterYield 102.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of methyl 2-aminobenzoate (50 g, 0.32 mol) in pyridine (250 mL) at 10-15° C., tosyl chloride (95 g, 0.5 mol) was added in portions. The reaction mixture was warmed to room temperature and allowed to stir for 2 h. The reaction mixture was poured on to ice and the precipitate filtered and washed with dilute hydrochloric acid (200 mL×2) followed by water (200 mL×2). The solid was dried under vacuo to afford methyl 2-(4-methylphenylsulfonamido)benzoate (100 g, 99%). 1H NMR: (400 MHz, DMDO-d6) δ: 10.41 (1H, s), 7.85 (1H, d, J=7.6 Hz), 7.69 (2H, d, J=8.0 Hz), 7.57 (1H, t, J=7.2 Hz), 7.45 (1H, d, J=8.0 Hz), 7.36 (2H, d, J=8.0 Hz), 7.18 (1H, t, J=7.6 Hz), 3.82 (3H, s), 2.25 (3H, s).

Workup

  1. additionThe reaction mixture was poured on to ice
  2. filtrationthe precipitate filtered
  3. washwashed with dilute hydrochloric acid (200 mL×2)
  4. customThe solid was dried under vacuo

Sources & evidence

ORD record
ord-df1e3ef8ff754117a4a5319216262b3c
Source dataset
uspto-grants-2012_09
Patent number
US08273754B2

Reaction notes

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