Potassium Hydroxide → HCID 66707185, compound

HRID 911743Notes

Reaction equation

HRID 911743 reaction equation
[OH-].[K+].[C:3]([O:7][C:8]([N:10]1[CH2:16][CH2:15][C:14]2[C:17]([S:22]C(=O)N(C)C)=[C:18]([Cl:21])[CH:19]=[CH:20][C:13]=2[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].Br[CH2:29][CH2:30][CH2:31][N:32]1[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[N:34](C(C)=C)[C:33]1=[O:44]>CO>[C:3]([O:7][C:8]([N:10]1[CH2:16][CH2:15][C:14]2[C:17]([S:22][CH2:29][CH2:30][CH2:31][N:32]3[C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=4[NH:34][C:33]3=[O:44])=[C:18]([Cl:21])[CH:19]=[CH:20][C:13]=2[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 576559793-tert-butoxycarbonyl-7-chloro-6-dimethylaminocarbonylthio-2,3,4,5-tetrahydro-1H-benzo[d]azepineHCID 576565691-(3-BroMopropyl)-1,3-dihydro-3-(1-Methylethenyl)-2H-benziMidazol-2-one

Product 1

HCID 66707185HCID 66707185, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add potassium hydroxide (933 mg, 16.6 mmol) in one portion to a solution of 3-tert-butoxycarbonyl-7-chloro-6-dimethylcarbamoylthio-2,3,4,5-tetrahydro-1H-benzo[d]azepine (200 mg, 0.52 mmol) in methanol (10 mL). Heat the reaction at reflux under nitrogen 4 h. Then cool to room temperature and add 1-(3-bromo-propyl)-3-isopropenyl-1,3-dihydro-benzoimidazol-2-one (142 mg, 0.52 mmol). Stir the reaction at room temperature overnight. Remove solvents in vacuo, extract into diethyl ether (2×50 mL), wash with water (2×50 mL) and brine (50 mL). Dry over MgSO4, filtrate and concentrate in vacuo to give 3-tert-butoxycarbonyl-7-chloro-6-[3-(2-oxo-2,3-dihydro-benzoimidazol-1-yl)-propylthio]-2,3,4,5-tetrahydro-1H-benzo[d]azepine as an oil (209 mg, 76%). MS (ES+) m/z: 550 (M+Na)+.

Workup

  1. temperatureHeat
  2. customthe reaction
  3. temperatureat reflux under nitrogen 4 h
  4. customthe reaction at room temperature overnight
  5. extractionRemove solvents in vacuo, extract into diethyl ether (2×50 mL)
  6. washwash with water (2×50 mL) and brine (50 mL)
  7. dry with materialDry over MgSO4, filtrate
  8. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-14df6e9cf10d413a9d76ed42b9e8eb23
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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