Triethylamine → 4-(N-(2-methoxybenzyl)sulfamoyl)phenyl acetate

HRID 658644Notes

Reaction equation

HRID 658644 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][NH2:24].C(N(CC)CC)C>ClCCl>[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11](=[O:13])(=[O:12])[NH:24][CH2:23][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[O:16][CH3:15])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 812922-MethoxybenzylamineHCID 129257104-(Chlorosulfonyl)phenyl acetate

Product 1

HCID 574223444-(N-(2-methoxybenzyl)sulfamoyl)phenyl acetateYield 97.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(chlorosulfonyl)phenyl acetate (example 5-42b) (531 mg, 2.265 mmol) in 5.0 mL of dichloromethane, was cooled to 0° C. in an ice bath. (2-methoxyphenyl)methanamine (325 μL, 2.492 mmol) and triethylamine (347 μL, 2.492 mmol) were added. The ice bath was then removed and the mixture warmed to ambient temperature and stirred for 2 hours. The reaction mixture was concentrated and the crude product was purified by column chromatography (hexanes/ethyl acetate=90/10 to 30/70) to afford pure 4-(N-(2-methoxybenzyl)sulfamoyl)phenyl acetate (743 mg, 89%) as a white solid. MS (M+H, 336.1) 1H NMR (400 MHz, CDCl3): δ, ppm: 2.32 (s, 3H), 3.71 (s, 3H), 4.18 (d, 2H, J=5.8 Hz), 5.15 (t, 1H, J=5.8 Hz), 6.71 (d, 1H, J=8.2 Hz), 6.82 (br t, 1H, J=7.4 Hz), 7.07 (br d, 1H, J=7.4 Hz), 7.10 (d, 2H, J=8.7 Hz), 7.19 (br t, 1H, J=7.8 Hz), 7.74 (d, 2H, J=8.7 Hz).

Workup

  1. customThe ice bath was then removed
  2. concentrationThe reaction mixture was concentrated
  3. customthe crude product was purified by column chromatography (hexanes/ethyl acetate=90/10 to 30/70)

Sources & evidence

ORD record
ord-4c04d4cfe28c4cd8a679f44f3e18468b
Source dataset
uspto-grants-2011_12
Patent number
US08076491B2

Reaction notes

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