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

HRID 30281
Notes
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Reaction equation

HRID 30281 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 800C 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-2996ca1e74824e76982146f3153ba8e9
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07423056B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes