Formic Acid → Ammonia

HRID 2054701Notes

Reaction equation

HRID 2054701 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]1[CH2:15][C@@H:14]2[CH2:16][C@H:11]1[CH2:12][NH:13]2.[CH2:17]=[O:18].[OH-:19].[Na+].[CH:21]([OH:23])=[O:22]>>[NH3:3].[C:21]([OH:23])(=[O:22])/[CH:4]=[CH:5]/[C:17]([OH:19])=[O:18].[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]1[CH2:15][C@@H:14]2[CH2:16][C@H:11]1[CH2:12][N:13]2[CH3:21]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 69213869HCID 69213869, compound

Product 2

HCID 222AmmoniaHCID 131726769HCID 131726769, compound

Procedure

A mixture of 2-(2-benzothiazolyl)-(1S,4S)-2,5-diazabicyclo-[2.2.1]-heptane (0.64 g; 2.77 mmol), formic acid (5 ml) and formaldehyde (5 ml) was stirred at reflux for 24 hours. Aqueous sodium hydroxide (50 ml; 1 M) was added and the mixture was extracted with dichloromethane (3×50 ml). Chromatography on silica gel with dichloromethane, methanol and conc. ammonia (89:10:1) gave the title compound as free base. Yield 0.19 g (28%). The corresponding salt was obtained by addition of a diethyl ether and methanol mixture (9:1) saturated with fumaric acid. Mp 170.8-181.0° C.

Workup

  1. temperatureat reflux for 24 hours
  2. extractionthe mixture was extracted with dichloromethane (3×50 ml)

Sources & evidence

ORD record
ord-746f4744b1164aaca1fec2b32b37e3ad
Source dataset
uspto-grants-2008_02
Patent number
US07329754B2

Reaction notes

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