Hydrochloric Acid → HCID 21995805, compound

HRID 1978559Notes

Reaction equation

HRID 1978559 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[S:17](=[O:19])(=[O:18])[CH2:16][CH2:15][C:14]([C:20]([NH:22][C:23]4[CH:28]=[CH:27][C:26]([CH2:29][N:30]([CH:32]5[CH2:37][CH2:36][C:35]6(OCC[O:38]6)[CH2:34][CH2:33]5)[CH3:31])=[CH:25][CH:24]=4)=[O:21])=[CH:13][C:12]=3[CH:42]=2)=[CH:4][CH:3]=1.Cl.C(=O)(O)[O-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[S:17](=[O:18])(=[O:19])[CH2:16][CH2:15][C:14]([C:20]([NH:22][C:23]4[CH:28]=[CH:27][C:26]([CH2:29][N:30]([CH3:31])[CH:32]5[CH2:37][CH2:36][C:35](=[O:38])[CH2:34][CH2:33]5)=[CH:25][CH:24]=4)=[O:21])=[CH:13][C:12]=3[CH:42]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 21995795HCID 21995795, compound

Product 1

HCID 21995805HCID 21995805, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-(4-chlorophenyl)-N-[4-[N-(4,4-ethylenedioxycyclohexyl)-N-methylaminomethyl]phenyl]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamide (180 mg) in THF (15 ml) was added at room temperature 3N hydrochloric acid (1 ml), and the mixture was stirred for 7 days. To the mixture was added saturated sodium bicarbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried with magnesium sulfate and concentrated under reduced pressure to give colorless solid, which was recrystallized from ethyl acetate to give colorless crystals of 7-(4-chlorophenyl)-N-[4-[N-methyl-N-(4-oxocyclohexyl)aminomethyl]phenyl]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamide (Compound 23) (85.9 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give colorless solid, which
  6. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-56a3f0f823964112b7e3206bcfe1a3a7
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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