N,N-Diethylethylenediamine → HCID 21450993, compound

HRID 596195Notes

Reaction equation

HRID 596195 reaction equation
[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][NH2:6])[CH3:2].[ClH:9].[Cl:10][C:11]([N:13]1[C:19]2[S:20][C:21]([CH2:23][CH3:24])=[CH:22][C:18]=2[C:17]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[Cl:31])=[N:16][CH2:15][CH2:14]1)=[O:12]>O1CCCC1>[OH2:12].[ClH:10].[ClH:9].[Cl:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[C:17]1[C:18]2[CH:22]=[C:21]([CH2:23][CH3:24])[S:20][C:19]=2[N:13]([C:11](=[O:12])[NH:6][CH2:5][CH2:4][N:3]([CH2:7][CH3:8])[CH2:1][CH3:2])[CH2:14][CH2:15][N:16]=1

Participants

4

Reactant 2

HCID 60993N,N-DiethylethylenediamineHCID 21451007HCID 21451007, compound

Product 1

HCID 21450993HCID 21450993, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 9.3 g of 2-diethylaminoethylamine in 50 ml of tetrahydrofuran is added 7.8 g of 1-chlorocarbonyl-5-o-chlorophenyl-7-ethyl-2,3-dihydro-1H-thieno[2,3-e][1,4]diazepine hydrochloride by portions with cooling and stirring. After the mixture is reacted for 2 hours at room temperature, the reaction substance is poured into 200 ml of ice-cold water and extracted with ethyl acetate. The organic layer is washed with water and dried over anhydrous sodium sulfate and then the solvent is evaporated under reduced pressure. The residue is treated with ethanolic hydrogen chloride to give 5-o-chlorophenyl-7-ethyl-1-(2-diethylaminoethylcarbamoyl)-2,3-dihydro-1H-thieno[2,3-e][1,4]diazepine dihydrochloride monohydrate as yellow crystals. This product, when recrystallized from a mixture of methanol and ethyl acetate, melts at 150°-151° C with decomposition.

Workup

  1. temperaturewith cooling
  2. customAfter the mixture is reacted for 2 hours at room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic layer is washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent is evaporated under reduced pressure
  7. additionThe residue is treated with ethanolic hydrogen chloride

Sources & evidence

ORD record
ord-2a8c097cf5b14bb5a6fc62dc036896cb
Source dataset
uspto-grants-1977_03
Patent number
US04010184

Reaction notes

Loading…