N,N-Diethylethylenediamine → Sematilide Hydrochloride

HRID 463676Notes

Reaction equation

HRID 463676 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([Cl:12])=[O:11])=[CH:8][CH:7]=1)(=[O:4])=[O:3].[CH2:15]([N:17]([CH2:21][CH3:22])[CH2:18][CH2:19][NH2:20])[CH3:16]>O1CCCC1>[ClH:12].[CH2:15]([N:17]([CH2:21][CH3:22])[CH2:18][CH2:19][NH:20][C:10](=[O:11])[C:9]1[CH:13]=[CH:14][C:6]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:7][CH:8]=1)[CH3:16]

Participants

4

Reactant 2

HCID 60993N,N-DiethylethylenediamineHCID 117911194-[(Methylsulfonyl)amino]benzoyl chloride

Product 1

HCID 58504Sematilide Hydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 100 ml of anhydrous tetrahydrofuran is added 10 g (0.0429 mole) of 4-[(methylsulfonyl)amino]benzoyl chloride and the reaction is cooled in an ice bath. A solution of 5.0 g (0.043 mole) of N,N-diethylethylenediamine in 25 ml of tetrahydrofuran is added over 15 minutes. The solvent is decanted and the precipitate is triturated with 100 ml of ether and crystallized from 100 ml of acetone with three drops of methanol. After cooling, the resultant solid is washed with acetone and dried in vacuo to provide the title compound.

Workup

  1. temperaturethe reaction is cooled in an ice bath
  2. customThe solvent is decanted
  3. customthe precipitate is triturated with 100 ml of ether
  4. customcrystallized from 100 ml of acetone with three drops of methanol
  5. temperatureAfter cooling
  6. washthe resultant solid is washed with acetone
  7. customdried in vacuo

Sources & evidence

ORD record
ord-e09fc756c34949f7a06131eb49b624ff
Source dataset
uspto-grants-1985_10
Patent number
US04544654

Reaction notes

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