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

HRID 1013402
Notes
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Reaction equation

HRID 1013402 reaction equation
C([N:8]1[CH2:16][CH2:15][CH:14]2[CH:10]([CH2:11][C:12]3[CH:19]=[CH:18][S:17][C:13]=32)[CH2:9]1)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].CC(Cl)OC(Cl)=O>ClC(Cl)C>[CH:19]1[C:12]2[CH2:11][CH:10]3[CH:14]([C:13]=2[S:17][CH:18]=1)[CH2:15][CH2:16][NH:8][CH2:9]3
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5213051-Chloroethyl chloroformateHCID 1317270426-Benzyl-4,5,6,7,7a,8-hexahydro-3bH-3-thia-6-aza-cyclopenta[alpha]indene

Product 1

HCID 862291074,5,6,7,7a,8-Hexahydro-3bH-3-thia-6-aza-cyclopenta[alpha]indeneYield 94%

Reagents, catalysts & solvents 1

HCID 63651,1-Dichloroethane
Solvent

Conditions

Temperature
22 °C

Procedure

The product of step f) (1.16 g, 4.3 mmol) in dichloroethane (21 ml) was treated with K2CO3 (2.38 g, 17.2 mmol) and Ace-Cl (1.86 ml, 17.2 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 hour at 22° C. The MeOH was concentrated and triturated with ether to give 874 mg (94%) 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-5005b302120f496ebc9c66fdd77c1ab4
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