Hydrochloric Acid → HCID 67399773, compound

HRID 711709Notes

Reaction equation

HRID 711709 reaction equation
[S:1]([NH:5][C:6]1[CH2:10][CH2:9][CH2:8][C:7]=1[C:11]#[N:12])(=[O:4])(=[O:3])[NH2:2].[OH-].[Na+].Cl>CCO>[NH:5]1[C:6]2[CH2:10][CH2:9][CH2:8][C:7]=2[C:11]([NH2:12])=[N:2][S:1]1(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67397635HCID 67397635, compound

Product 1

HCID 67399773HCID 67399773, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-sulfamoylaminocyclopent-1-enecarbonitrile (Example 107a) (108 mg, 0.57 mmol) in EtOH was treated with NaOH (2.0 N, 0.5 mL), and the resultant solution was heated to 100° C. and stirred at that temperature for 4 h. After it was cooled down to room temperature, the reaction solution was carefully neutralized with 2N HCl while it was vigorously stirred at 0° C. The reaction solution was dried down under vacuum, and the residue was purified by chromatography on silica gel eluting with 10% MeOH in dichloromethane to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ 1.69-1.63 (m, 2H), 2.2 (t, J=7.6 Hz, 2H), 2.3 (t, J=6.8 Hz, 2H), 5.12 (s, 2H). MS 188 (MH+).

Workup

  1. stirringwas vigorously stirred at 0° C
  2. customThe reaction solution was dried down under vacuum
  3. customthe residue was purified by chromatography on silica gel eluting with 10% MeOH in dichloromethane

Sources & evidence

ORD record
ord-f3f293a10c814e079410b05d35c9aa6b
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

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