Dimethylamine → HCID 21451012, compound

HRID 596190Notes

Reaction equation

HRID 596190 reaction equation
[Cl:1][C:2]([N:4]1[C:10]2[S:11][C:12]([CH2:14][CH3:15])=[CH:13][C:9]=2[C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])=[N:7][CH2:6][CH2:5]1)=[O:3].[CH2:23]([N:25](CC)[CH2:26]C)C.CNC.O>O1CCCC1>[ClH:1].[Cl:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:8]1[C:9]2[CH:13]=[C:12]([CH2:14][CH3:15])[S:11][C:10]=2[N:4]([C:2](=[O:3])[N:25]([CH3:26])[CH3:23])[CH2:5][CH2:6][N:7]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 962WaterHCID 8471TriethylamineHCID 21451001HCID 21451001, compound

Product 1

HCID 21451012HCID 21451012, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 8.7 g of 1-chlorocarbonyl-5-o-chlorophenyl-7-ethyl-2,3-dihydro-1H-thieno[2,3-e][1,4]diazepine and 2.8 g of triethylamine in 50 ml of tetrahydrofuran is added dropwise 50 ml of 25%(W/V) tetrahydrofuran solution of dimethylamine with stirring. The whole mixture is refluxed with stirring for 2 hours, and then cooled and transferred to water. The resultant solution is extracted with ethyl acetate, washed with water and dried over anhydrous magnesium sulfate. The solvent is evaporated under reduced pressure. The residue is treated with ethanolic hydrogen chloride to give 5-o-chlorophenyl-7-ethyl-1-dimethylcarbamoyl-2,3-dihydro-1H-thieno[2,3-e][1,4]diazepine hydrochloride as yellow crystals. This product, when recrystallized from a mixture of methanol and ethyl acetate, melts at 240°-241° C with decomposition.

Workup

  1. temperatureThe whole mixture is refluxed
  2. stirringwith stirring for 2 hours
  3. temperaturecooled
  4. extractionThe resultant solution is extracted with ethyl acetate
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent is evaporated under reduced pressure
  8. additionThe residue is treated with ethanolic hydrogen chloride

Sources & evidence

ORD record
ord-fc4e8cf96133467d82d85f64256b7ffa
Source dataset
uspto-grants-1977_03
Patent number
US04010184

Reaction notes

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