Water → HCID 21451012, compound

HRID 596189Notes

Reaction equation

HRID 596189 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[CH:17]=[C:16]([CH2:18][CH3:19])[S:15][C:10]=2[NH:11][CH2:12][CH2:13][N:14]=1.C(N(CC)CC)C.[CH3:27][N:28]([CH3:32])[C:29](Cl)=[O:30].O>O1CCCC1>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[CH:17]=[C:16]([CH2:18][CH3:19])[S:15][C:10]=2[N:11]([C:29](=[O:30])[N:28]([CH3:32])[CH3:27])[CH2:12][CH2:13][N:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 135967971HCID 135967971, compound

Product 1

HCID 21451012HCID 21451012, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 32 g of 5-o-chlorophenyl-7-ethyl-2,3-dihydro-1H-thieno[2,3-e][1,4]diazepine in 100 ml of tetrahydrofuran is added 12.5 g of triethylamine, and then to this solution is added dropwise a solution of 13.2 g of dimethylcarbamoyl chloride in 30 ml of tetrahydrofuran with stirring. The whole mixture is stirred under reflux for 6 hours. After cooling, the reaction solution is transferred to water, and extracted with ethyl acetate. After the organic layer is 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. stirringThe whole mixture is stirred
  2. temperatureunder reflux for 6 hours
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate
  5. washAfter the organic layer is washed 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-0f6bedd0d74543fc8f55a815bc445eb3
Source dataset
uspto-grants-1977_03
Patent number
US04010184

Reaction notes

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