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Potassium Carbonate → 4,5,6,7,7a,8-Hexahydro-3bH-1-thia-5-aza-cyclopenta[alpha]indene

HRID 1013394
Notes
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Reaction equation

HRID 1013394 reaction equation
C([N:8]1[CH2:16][CH:15]2[CH:11]([CH2:12][C:13]3[S:19][CH:18]=[CH:17][C:14]=32)[CH2:10][CH2:9]1)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].CC(Cl)OC(Cl)=O>ClC(Cl)C>[S:19]1[C:13]2[CH2:12][CH:11]3[CH:15]([C:14]=2[CH:17]=[CH:18]1)[CH2:16][NH:8][CH2:9][CH2:10]3
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5213051-Chloroethyl chloroformateHCID 672051085-Benzyl-4,5,6,7,7a,8-hexahydro-3bH-1-thia-5-aza-cyclopenta[alpha]indene

Product 1

HCID 689024214,5,6,7,7a,8-Hexahydro-3bH-1-thia-5-aza-cyclopenta[alpha]indeneYield 61%

Reagents, catalysts & solvents 1

HCID 63651,1-Dichloroethane
Solvent

Conditions

Temperature
22 °C

Procedure

The product from step g) (963 mg, 3.58 mmol) in dichloroethane (18 ml) was treated with K2CO3 (1.97 g, 14.3 mmol) and Ace-Cl (1.54 ml, 14.3 mmol) at 80° C. for 16 hours. Next, the reaction mixture was filtered, concentrated and the residue was dissolved in anhydrous MeOH (25 ml) and stirred for 1 h at 22° C. The MeOH was concentrated and triturated with ether to give 467 mg (61%) of the subtitle compound. MS calculated for C10H13NS+H 180, observed 180.

Workup

  1. filtrationNext, the reaction mixture was filtered
  2. concentrationconcentrated
  3. dissolutionthe residue was dissolved in anhydrous MeOH (25 ml)
  4. concentrationThe MeOH was concentrated
  5. customtriturated with ether

Sources & evidence

ORD record
ord-0c1ca1f974824793865d30153523bc10
Source dataset
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07981919B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes