Ethyl Bromide → HCID 21998542, compound

HRID 1976531Notes

Reaction equation

HRID 1976531 reaction equation
[K].[C:2]([NH:6][S:7]([C:10]1[CH:18]=[C:17]([C:19](=[O:23])[N:20]([CH3:22])[CH3:21])[CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=[O:13])(=[O:9])=[O:8])([CH3:5])([CH3:4])[CH3:3].Br[CH2:25][CH3:26]>C(#N)C.C(OCC)(=O)C>[C:2]([NH:6][S:7]([C:10]1[CH:18]=[C:17]([C:19](=[O:23])[N:20]([CH3:21])[CH3:22])[CH:16]=[CH:15][C:11]=1[C:12]([O:14][CH2:25][CH3:26])=[O:13])(=[O:9])=[O:8])([CH3:5])([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 6332Ethyl BromideHCID 5462222PotassiumHCID 21998539HCID 21998539, compound

Product 1

HCID 21998542HCID 21998542, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 3.0 g (8.2 mmol) of the potassium salt of 2-tert-butylsulfamoyl-4-dimethylcarbamoylbenzoic acid, and 0.21 g (0.79 mmol) of 1,4,7,10,13,16-hexaoxacyclooctane in 25 ml of acetonitrile was stirred at room temperature for half an hour, and 890 mg (8.2 mmol) of bromoethane were then added. The mixture was subsequently heated under reflux for 6 h and then allowed to cool to room temperature. For work-up, the reaction mixture was diluted with ethyl acetate and extracted with 1 M aqueous hydrochloric acid solution, saturated aqueous sodium bicarbonate solution and water. The organic phase was dried over sodium sulfate, filtered off and concentrated. This gave 2.31 g (79% of theory) of ethyl 2-tert-butylsulfamoyl-4-dimethylcarbamoylbenzoate as a colorless solid of m.p. 101 to 102.5° C.

Workup

  1. temperatureThe mixture was subsequently heated
  2. temperatureunder reflux for 6 h
  3. temperatureto cool to room temperature
  4. extractionextracted with 1 M aqueous hydrochloric acid solution, saturated aqueous sodium bicarbonate solution and water
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. filtrationfiltered off
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4b7c82d1fd3c4ca3b0769c80a0cc9a83
Source dataset
uspto-grants-2001_05
Patent number
US06228808B1

Reaction notes

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