N,N-Dimethylethylenediamine → HCID 86734518, compound

HRID 596196Notes

Reaction equation

HRID 596196 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH2:5].Cl.Cl[C:9]([N:11]1[C:17]2[S:18][C:19]([CH2:21][CH3:22])=[CH:20][C:16]=2[C:15]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:29])=[N:14][CH2:13][CH2:12]1)=[O:10]>O1CCCC1>[Cl:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:15]1[C:16]2[CH:20]=[C:19]([CH2:21][CH3:22])[S:18][C:17]=2[N:11]([C:9](=[O:10])[NH:5][CH2:4][CH2:3][N:2]([CH3:6])[CH3:1])[CH2:12][CH2:13][N:14]=1

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 21451007HCID 21451007, compound

Product 1

HCID 86734518HCID 86734518, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7.1 g of 2-dimethylaminoethylamine in 40 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 one and half 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-dimethylaminoethylcarbamoyl)-2,3-dihydro-1H-thieno[2,3-e][1,4]diazepine dihydrochloric monohydrate as yellow crystals. This product, when recrystallized from a mixture of methanol and ethyl acetate, melts at 160°-162° C with decomposition.

Workup

  1. temperaturewith cooling
  2. customAfter the mixture is reacted for one and half 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-3fe85c8386204b8ab39b6c38099a85d1
Source dataset
uspto-grants-1977_03
Patent number
US04010184

Reaction notes

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