Dimethylformamide dimethyl acetal → 2-chloro-4-(N-((dimethylamino)methylene)sulfamoyl)-6-fluorobenzyl acetate

HRID 83906Notes

Reaction equation

HRID 83906 reaction equation
[C:1]([O:4][CH2:5][C:6]1[C:11]([F:12])=[CH:10][C:9]([S:13](=[O:16])(=[O:15])[NH2:14])=[CH:8][C:7]=1[Cl:17])(=[O:3])[CH3:2].CO[CH:20](OC)[N:21]([CH3:23])[CH3:22]>CC#N>[C:1]([O:4][CH2:5][C:6]1[C:11]([F:12])=[CH:10][C:9]([S:13](=[O:15])(=[O:16])[N:14]=[CH:20][N:21]([CH3:23])[CH3:22])=[CH:8][C:7]=1[Cl:17])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 667401992-Chloro-6-fluoro-4-sulfamoylbenzyl acetate

Product 1

HCID 667410382-chloro-4-(N-((dimethylamino)methylene)sulfamoyl)-6-fluorobenzyl acetateYield 76%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-chloro-6-fluoro-4-sulfamoylbenzyl acetate (1 g, 3.6 mmol) in CH3CN (20 mL2) at 0° C. under N2 was added 1,1-dimethoxy-N,N-dimethylmethanamine (0.7 ml, 5.4 mmol). The resulting solution was stirred at room temperature 1 h, concentrated under reduced pressure, and purified by column chromatography (DCM/EtOAc=9:1) to afford 2-chloro-4-(N-((dimethylamino)methylene)sulfamoyl)-6-fluorobenzyl acetate (850 mg, 76%) as ivory solid. 1H NMR (400 MHz, CDCl3) δ 8.12 (s, 1H), 7.76 (s, 1H), 7.55 (d, 1H), 5.26 (s, 2H), 3.18 (s, 3H), 3.05 (s, 3H), 2.08 (s, 3H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. custompurified by column chromatography (DCM/EtOAc=9:1)

Sources & evidence

ORD record
ord-f2c17582a5ea4d7fac5f5aed82bfee96
Source dataset
uspto-grants-2014_09
Patent number
US08846739B2

Reaction notes

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