Hydrochloric Acid → HCID 14208733, compound

HRID 1040608Notes

Reaction equation

HRID 1040608 reaction equation
CS(O[CH2:6][CH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]([CH2:16]OS(C)(=O)=O)[O:8]1)(=O)=O.[NH4+:22].[OH-].Cl>C(#N)C>[CH:9]12[O:8][CH:7]([CH2:6][NH:22][CH2:16]1)[C:15]1[C:10]2=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 14770434HCID 14770434, compound

Product 1

HCID 14208733HCID 14208733, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

Methanesulfonic acid 3-methanesulfonyloxymethyl-1,3-dihydro-isobenzofuran-1-ylmethyl ester (12.1 g, 36 mmol) and conc. NH4OH (50 mL) was dissolved in acetonitrile (100 mL) and heated at 100° C. in a sealed vessel for 2 h. The reaction was then cooled, adjusted to pH 5-6 with 1 N HCl and extracted with diethyl ether (100 mL). The aqueous layer was then basified with 10 N NaOH and extracted with diethyl ether (2×100 mL). The later organic layer was dried over MgSO4, filtered, concentrated and purified with silica gel chromatography (0-15% MeOH in CH2Cl2) to obtain 12-Oxa-10-aza-tricyclo[6.3.1.0*2,7*]dodeca-2,4,6-triene as a brown, viscous oil (5.1 g, 88%). MS (m/e) 162 (M+1); HPLC (93%)

Workup

  1. temperatureThe reaction was then cooled
  2. extractionextracted with diethyl ether (100 mL)
  3. extractionextracted with diethyl ether (2×100 mL)
  4. dry with materialThe later organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified with silica gel chromatography (0-15% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-cdc75994b9164f508d17bc1940f49912
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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