Potassium Carbonate → Hydrochloric Acid

HRID 30288

Reaction equation

HRID 30288 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH3:7][CH:8]1[C:15]2[S:14][CH:13]=[CH:12][C:11]=2[CH:10]2[CH2:16][N:17](C(C3C=CC=CC=3)C)[CH2:18][CH:9]12.[Cl:27]CCOC(Cl)=O>CO>[CH3:7][CH:8]1[C:15]2[S:14][CH:13]=[CH:12][C:11]=2[CH:10]2[CH2:16][NH:17][CH2:18][CH:9]12.[ClH:27]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 123052-Chloroethyl chloroformateHCID 1317270457-Methyl-5-(1-phenyl-ethyl)-3b,4,5,6,6a,7-hexahydro-1-thia-5-aza-cyclopenta[alpha]pentalene

Product 2

HCID 313Hydrochloric AcidHCID 597894257-Methyl-3b,4,5,6,6a,7-hexahydro-1-thia-5-aza-cyclopenta[alpha]pentalene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

K2CO3 (320 mg, 2.32 mmol) was added to a solution of the product from step g) (165 mg, 0.58 mmol) in 6 mL followed by the addition of 2-chloroethylchloroformate (332 mg, 2.32 mmol) under vigorous stirring at room temperature. Next, the reaction was stirred for two hours at 75° C. after which the reaction mixture was cooled, filtered and the solvent was evaporated to leave an oily residue that was then dissolved in dry methanol (10 mL) and was stirred at room temperature for one hour. The solvent was evaporated and the residue was triturated in diethyl ether (5 mL) to give the subtitle compound as its HCl salt. MS calculated for C10H13NS+H: 180, observed: 180. 1H NMR (CDCl3300 MHz) δ 1.32 (d, 3H), 1.93 (s, 1H), 3.04 (m, 1H), 3.18 (m, 2H), 3.47 (m, 3H), 3.78 (m, 1H), 6.83 (d, 1H), 7.21 (d, 1H) ppm.

Workup

  1. stirringNext, the reaction was stirred for two hours at 75° C. after which the reaction mixture
  2. temperaturewas cooled
  3. filtrationfiltered
  4. customthe solvent was evaporated
  5. customto leave an oily residue that
  6. stirringwas stirred at room temperature for one hour
  7. customThe solvent was evaporated
  8. customthe residue was triturated in diethyl ether (5 mL)

Sources & evidence

ORD record
ord-85d41e6f25a74b478ea7ed29ef94133e
Source dataset
uspto-grants-2008_09
Patent number
US07423056B2

Linked notes

Loading…