Triethylamine → Methyl 4-(N-(4-methoxybenzyl)sulfamoyl)benzoate

HRID 548041Notes

Reaction equation

HRID 548041 reaction equation
Cl[S:2]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][NH2:24])=[CH:19][CH:18]=1.C(N(CC)CC)C>ClCCl>[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][NH:24][S:2]([C:5]2[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=2)(=[O:4])=[O:3])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 754524-MethoxybenzylamineHCID 4738388Methyl 4-(Chlorosulfonyl)benzoate

Product 1

HCID 26527056Methyl 4-(N-(4-methoxybenzyl)sulfamoyl)benzoateYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4-(chlorosulfonyl)benzoate (Example 5-10c) (4 g, 17.09 mmol) in dichloromethane (40 mL) at 0° C. in an ice bath, was added (4-methoxyphenyl)methanamine (2.56 mL, 19.65 mmol) and triethylamine (2.38 mL, 17.1 mmol). The ice bath was then removed and the mixture was allowed to warm to ambient temperature with stirring for an additional 2 hours. Upon completion (monitored by TLC 40% ethyl acetate/hexanes), the solvent was removed in vacuo. The residue was re-dissolved in ethyl acetate (200 mL), washed with 1N HCl (aq, 20 mL), water (20 mL) and brine (20 mL) then dried over magnesium sulfate. The solution was concentrated and the product purified by re-crystallization with hot ethyl acetate/hexanes to afford pure methyl 4-(N-(4-methoxybenzyl)sulfamoyl)benzoate (4.3 g, 74.8%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ, ppm: 3.67 (s, 3H), 3.78 (s, 3H), 3.93 (s, 2H), 6.78 (m, 2H), 7.09 (m, 2H), 7.87 (m, 2H), 8.08 (m, 2H), 8.25 (br, s, 1H).

Workup

  1. customThe ice bath was then removed
  2. customUpon completion (monitored by TLC 40% ethyl acetate/hexanes), the solvent was removed in vacuo
  3. dissolutionThe residue was re-dissolved in ethyl acetate (200 mL)
  4. washwashed with 1N HCl (aq, 20 mL), water (20 mL) and brine (20 mL)
  5. dry with materialthen dried over magnesium sulfate
  6. concentrationThe solution was concentrated
  7. customthe product purified by re-crystallization with hot ethyl acetate/hexanes

Sources & evidence

ORD record
ord-c2c17b9992524fa888c8eef3330e07a6
Source dataset
uspto-grants-2011_05
Patent number
US07939671B2

Reaction notes

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