Ethyl isocyanate → 3-ethylcarbamoyl-2,3,4,5-tetrahydro-1H-3-benzazepine-7-sulfonamide

HRID 2398168Notes

Reaction equation

HRID 2398168 reaction equation
[CH2:1]1[C:7]2[CH:8]=[CH:9][C:10]([S:12]([NH2:15])(=[O:14])=[O:13])=[CH:11][C:6]=2[CH2:5][CH2:4][NH:3][CH2:2]1.[CH2:16]([N:18]=[C:19]=[O:20])[CH3:17]>CN(C)C=O>[CH2:16]([NH:18][C:19]([N:3]1[CH2:2][CH2:1][C:7]2[CH:8]=[CH:9][C:10]([S:12]([NH2:15])(=[O:14])=[O:13])=[CH:11][C:6]=2[CH2:5][CH2:4]1)=[O:20])[CH3:17]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 212429322,3,4,5-tetrahydro-1H-3-benzazepine-7-sulfonamide

Product 1

HCID 214344333-ethylcarbamoyl-2,3,4,5-tetrahydro-1H-3-benzazepine-7-sulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.4 G. of 2,3,4,5-tetrahydro-1H-3-benzazepine-7-sulfonamide are dissolved in 50 ml. of dimethylformamide while warming at 60° C. and the solution is then rapidly cooled with an icebath. As soon as a temperature of 20° C. is reached, 1.18 ml. of ethylisocyanate are added dropwise while stirring, and the mixture is subsequently stirred at 25° C. for 0.5 hour. The solution is then concentrated in vacuo on a bath at 80° C. and the crystalline residue is digested with ether. There is obtained 3-ethylcarbamoyl-2,3,4,5-tetrahydro-1H-3-benzazepine-7-sulfonamide.

Workup

  1. temperaturethe solution is then rapidly cooled with an icebath
  2. customsoon as a temperature of 20° C.
  3. stirringthe mixture is subsequently stirred at 25° C. for 0.5 hour
  4. concentrationThe solution is then concentrated in vacuo on a bath at 80° C.

Sources & evidence

ORD record
ord-e22027093965495ba34ddd7fe695f6cd
Source dataset
uspto-grants-1977_05
Patent number
US04024128

Reaction notes

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