Water → HCID 21450985, compound

HRID 596200Notes

Reaction equation

HRID 596200 reaction equation
[CH2:1]([C:3]1[S:19][C:6]2[NH:7][CH2:8][CH2:9][N:10]=[C:11]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[C:5]=2[CH:4]=1)[CH3:2].C(N(CC)CC)C.[CH3:27][N:28]([CH3:32])[C:29]([Cl:31])=[O:30].O>O1CCCC1>[ClH:31].[CH2:1]([C:3]1[S:19][C:6]2[N:7]([C:29](=[O:30])[N:28]([CH3:32])[CH3:27])[CH2:8][CH2:9][N:10]=[C:11]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[C:5]=2[CH:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 136014055HCID 136014055, compound

Product 1

HCID 21450985HCID 21450985, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5.5 g of 7-ethyl-5-p-fluorophenyl-2,3-dihydro-1H-thieno[2,3-e][1,4]diazepine in 50 ml of tetrahydrofuran is added 2.2 g of triethylamine, and then to this solution is added dropwise a solution of 2.4 g of dimethylcarbamoyl chloride in 10 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 7-ethyl-5-p-fluorophenyl-1-dimethylcarbamoyl-2,3-dihydro-1H-thieno[2,3-e][1,4]diazepine hydrochloride as pale yellow crystals. This product, when recrystallized from ethanol, melts at 216°-218° 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-ded4c1960a4e4e3f8f66b9293e8791ab
Source dataset
uspto-grants-1977_03
Patent number
US04010184

Reaction notes

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