Tetrahydrofuran → 4-sulfamoyl-N-(2-dimethylaminoethyl)benzamide

HRID 215757Notes

Reaction equation

HRID 215757 reaction equation
CNN(CC)NC.C([N:10]([CH2:13][CH3:14])[CH2:11][CH3:12])C.[CH:15]([N:18]([CH:21](C)C)CC)(C)C.[S:24]([C:28]1[CH:36]=[CH:35]C=C[C:29]=1[C:30](Cl)=O)(=[O:27])(=[O:26])[NH2:25].[O:37]1CCCC1>CCOCC.CCCCCC>[S:24]([C:28]1[CH:36]=[CH:35][C:14]([C:13]([NH:10][CH2:11][CH2:12][N:18]([CH3:21])[CH3:15])=[O:37])=[CH:30][CH:29]=1)(=[O:27])(=[O:26])[NH2:25]

Participants

8

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 81531DiisopropylethylamineHCID 54563777Sulfamoylbenzoyl chlorideHCID 57041336N,N-Dimethylaminoethylamine

Product 1

HCID 250600504-sulfamoyl-N-(2-dimethylaminoethyl)benzamideYield 48%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

To the 250 ml 3 neck flask equipped with the thermometer, the add funnel and the stirrer, 40 ml of tetrahydrofurane or ether, 4.3 g (0.0485 mol) of N,N-dimethylaminoethylamine and 24 g (33 ml) (0.238 mol) of triethylamine or DIPEA (diisopropylethylamine) was taken up. The solution was cooled to 0° C. and the solution of 10.3 g (0.0470 mol) of sulfamoylbenzoyl chloride IX in 60 ml tetrahydrofurane or ether was added dropwise for 30 min under cooling and stirring so as the temperature did not exceed 0 to 15° C. The mixture was then stirred for 12 hours the at room temperature. 100 ml of petroleum ether or hexane was added to the mixture. The semi-solid product was filtered off and macerated with 20 ml of ice-cooled saturated aqueous sodium chloride solution. The solid product was separated, washed once with 10 ml saturated aqueous sodium chloride solution, 2 times with ice water and purified with crystallization from the water:ethanol (2:1). Afforded 6.1 g (48.0%) of 4-sulfamoyl-N-(2-dimethylaminoethyl)benzamide 1′-1. Colourless solid, m.p. 150-151° C.

Workup

  1. temperatureunder cooling
  2. customdid not exceed 0 to 15° C
  3. stirringThe mixture was then stirred for 12 hours the at room temperature
  4. filtrationThe semi-solid product was filtered off
  5. temperaturecooled saturated aqueous sodium chloride solution
  6. customThe solid product was separated
  7. washwashed once with 10 ml saturated aqueous sodium chloride solution, 2 times with ice water
  8. custompurified with crystallization from the water:ethanol (2:1)

Sources & evidence

ORD record
ord-7e4741819063461a8090a281fcffa361
Source dataset
uspto-grants-2012_06
Patent number
US08193184B2

Reaction notes

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